KR102732835B1 - 파르네소이드 x 수용체 조정제로서의 가교된 비시클릭 화합물 - Google Patents
파르네소이드 x 수용체 조정제로서의 가교된 비시클릭 화합물 Download PDFInfo
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- KR102732835B1 KR102732835B1 KR1020207015270A KR20207015270A KR102732835B1 KR 102732835 B1 KR102732835 B1 KR 102732835B1 KR 1020207015270 A KR1020207015270 A KR 1020207015270A KR 20207015270 A KR20207015270 A KR 20207015270A KR 102732835 B1 KR102732835 B1 KR 102732835B1
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- methoxy
- cyclopropyl
- isoxazol
- octan
- bicyclo
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- 125000002619 bicyclic group Chemical group 0.000 title claims description 7
- 102100038495 Bile acid receptor Human genes 0.000 title abstract description 85
- 101000603876 Homo sapiens Bile acid receptor Proteins 0.000 title abstract description 85
- 150000001875 compounds Chemical class 0.000 claims abstract description 294
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 65
- 150000003839 salts Chemical class 0.000 claims abstract description 55
- 239000012453 solvate Substances 0.000 claims abstract description 37
- 206010016654 Fibrosis Diseases 0.000 claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 27
- 201000010099 disease Diseases 0.000 claims abstract description 25
- 230000004761 fibrosis Effects 0.000 claims abstract description 25
- 230000001575 pathological effect Effects 0.000 claims abstract description 4
- -1 1,5-naphthyridinyl Chemical group 0.000 claims description 247
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 38
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 36
- 239000005711 Benzoic acid Substances 0.000 claims description 34
- 235000010233 benzoic acid Nutrition 0.000 claims description 34
- 125000003566 oxetanyl group Chemical group 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 21
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 14
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 14
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 13
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 239000003937 drug carrier Substances 0.000 claims description 13
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 13
- 125000002757 morpholinyl group Chemical group 0.000 claims description 13
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 13
- 125000004193 piperazinyl group Chemical group 0.000 claims description 12
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 12
- 125000002393 azetidinyl group Chemical group 0.000 claims description 11
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 10
- 238000002560 therapeutic procedure Methods 0.000 claims description 10
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 9
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 9
- 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims description 8
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 7
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 7
- 201000002793 renal fibrosis Diseases 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 208000020832 chronic kidney disease Diseases 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- MSKHYVHBBFEAMY-BQYQJAHWSA-N 2-[4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]phenyl]acetic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)/C=C/C1=CC=C(C=C1)CC(=O)O MSKHYVHBBFEAMY-BQYQJAHWSA-N 0.000 claims description 5
- MJLYHUGEXSTFAI-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F MJLYHUGEXSTFAI-UHFFFAOYSA-N 0.000 claims description 5
- OEFRRNDOWOKWSE-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-6-cyclopropyloxypyridine-2-carboxylic acid Chemical compound C1(CC1)OC1=CC(=CC(=N1)C(=O)O)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC=1C(=NOC=1C1CC1)C1=C(C=NC=C1Cl)Cl OEFRRNDOWOKWSE-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 208000010157 sclerosing cholangitis Diseases 0.000 claims description 5
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 4
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 4
- 230000009787 cardiac fibrosis Effects 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- KNOCEIYOPWHYEO-UHFFFAOYSA-N 1-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methyl]pyrazole-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)CN1N=CC(=C1)C(=O)O KNOCEIYOPWHYEO-UHFFFAOYSA-N 0.000 claims description 3
- HYRHTCHZQGGIKB-UHFFFAOYSA-N 2-[2-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyridin-4-yl]acetic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=NC=CC(=C1)CC(=O)O HYRHTCHZQGGIKB-UHFFFAOYSA-N 0.000 claims description 3
- OKIYJIPJCMIEJY-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,3-benzothiazole-7-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12CCC(CC1)(CC2)C=1SC2=C(N=1)C=CC=C2C(=O)O OKIYJIPJCMIEJY-UHFFFAOYSA-N 0.000 claims description 3
- SGUJKFFAWLLIGZ-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,3-oxazole-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12CCC(CC1)(CC2)C=1OC=C(N=1)C(=O)O SGUJKFFAWLLIGZ-UHFFFAOYSA-N 0.000 claims description 3
- ORGFARYSIXOFLS-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-5-(trifluoromethyl)-1,3-benzothiazole-7-carboxamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1SC2=C(N=1)C=C(C=C2C(=O)N)C(F)(F)F ORGFARYSIXOFLS-UHFFFAOYSA-N 0.000 claims description 3
- PXUKANRLSFFNRC-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)C(F)(F)F)COC12CCC(CC1)(CC2)C=1SC2=C(N=1)C=CC(=C2)C(=O)O PXUKANRLSFFNRC-UHFFFAOYSA-N 0.000 claims description 3
- BQZVTXZADJYSTG-UHFFFAOYSA-N 2-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]acetic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)CC(=O)O BQZVTXZADJYSTG-UHFFFAOYSA-N 0.000 claims description 3
- DBZIYVDYGIFKFQ-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-hydroxymethyl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F)O DBZIYVDYGIFKFQ-UHFFFAOYSA-N 0.000 claims description 3
- PAOITBRBSLDZKC-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]methoxy]-1,3-thiazole-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12CCC(CC1)(CC2)COC=1SC=C(N=1)C(=O)O PAOITBRBSLDZKC-UHFFFAOYSA-N 0.000 claims description 3
- XUKKVJLGZVCGLP-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C#CC=1C=C(C(=O)O)C=CC=1 XUKKVJLGZVCGLP-UHFFFAOYSA-N 0.000 claims description 3
- WPGMGJQJZMZVPU-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-6-fluoroimidazo[1,2-a]pyridine-8-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C#CC1=CN=C2N1C=C(C=C2C(=O)O)F WPGMGJQJZMZVPU-UHFFFAOYSA-N 0.000 claims description 3
- WPNCTCCEACQUDU-UHFFFAOYSA-N 3-[4-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]triazol-1-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1N=NN(C=1)C=1C=C(C(=O)O)C=CC=1 WPNCTCCEACQUDU-UHFFFAOYSA-N 0.000 claims description 3
- MWOZFTAXBUAODT-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2,6-difluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C(=C(C(=O)O)C(=CC=1)F)F MWOZFTAXBUAODT-UHFFFAOYSA-N 0.000 claims description 3
- KPNRGTCZVFGEMY-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1 KPNRGTCZVFGEMY-UHFFFAOYSA-N 0.000 claims description 3
- MCNALCXWQXEAJX-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1 MCNALCXWQXEAJX-UHFFFAOYSA-N 0.000 claims description 3
- JKMJWOGBGIGBGG-UHFFFAOYSA-N 3-[5-[4-[[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]amino]methyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)NCC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1 JKMJWOGBGIGBGG-UHFFFAOYSA-N 0.000 claims description 3
- ZPFDGMFKVKTCSJ-UHFFFAOYSA-N 3-chloro-4-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]bicyclo[2.2.2]octane-1-carbonyl]amino]benzoic acid Chemical compound ClC=1C=C(C(=O)O)C=CC=1NC(=O)C12CCC(CC1)(CC2)COCC=1C(=NOC=1C1CC1)C1=C(C=CC=C1Cl)Cl ZPFDGMFKVKTCSJ-UHFFFAOYSA-N 0.000 claims description 3
- RIFGMDROEVYTMA-UHFFFAOYSA-N 3-chloro-4-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]bicyclo[2.2.2]octane-1-carbothioyl]amino]benzoic acid Chemical compound ClC=1C=C(C(=O)O)C=CC=1NC(=S)C12CCC(CC1)(CC2)COCC=1C(=NOC=1C1CC1)C1=C(C=CC=C1Cl)Cl RIFGMDROEVYTMA-UHFFFAOYSA-N 0.000 claims description 3
- MMYAZTHOHJSTKC-UHFFFAOYSA-N 4-(1-chloro-3-hydroxypropan-2-yl)oxy-6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]quinoline-2-carboxylic acid Chemical compound ClCC(CO)OC1=CC(=NC2=CC=C(C=C12)OCC12CCC(CC1)(CC2)OCC=1C(=NOC=1C1CC1)C1=C(C=NC=C1Cl)Cl)C(=O)O MMYAZTHOHJSTKC-UHFFFAOYSA-N 0.000 claims description 3
- VLDXYEYYQPWZHV-UHFFFAOYSA-N 4-[4-[[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]amino]methyl]-2-oxabicyclo[2.2.2]octan-1-yl]benzamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)NCC12COC(CC1)(CC2)C1=CC=C(C(=O)N)C=C1 VLDXYEYYQPWZHV-UHFFFAOYSA-N 0.000 claims description 3
- NYFKOGMAHZAFET-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-N-methylsulfonylbenzamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C1=CC=C(C(=O)NS(=O)(=O)C)C=C1 NYFKOGMAHZAFET-UHFFFAOYSA-N 0.000 claims description 3
- AJHHQPYCALNQJL-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)COC12CCC(CC1)(CC2)C1=NC(=NO1)C1=CC=C(C(=O)O)C=C1 AJHHQPYCALNQJL-UHFFFAOYSA-N 0.000 claims description 3
- OGENKUKIJQYNGK-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)COCC12COC(CC1)(CC2)C1=NC(=NO1)C1=CC=C(C(=O)O)C=C1 OGENKUKIJQYNGK-UHFFFAOYSA-N 0.000 claims description 3
- UXTOVNAWKRFEQM-UHFFFAOYSA-N 4-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]isoquinoline-1-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=CN=C(C2=CC=CC=C12)C(=O)O UXTOVNAWKRFEQM-UHFFFAOYSA-N 0.000 claims description 3
- RPJVJLNMEAKYTJ-UHFFFAOYSA-N 4-cyclopropyl-6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=CC(=NC2=CC=C(C=C12)OCC12CCC(CC1)(CC2)OCC=1C(=NOC=1C1CC1)C1=C(C=NC=C1Cl)Cl)C(=O)O RPJVJLNMEAKYTJ-UHFFFAOYSA-N 0.000 claims description 3
- YDLTVBMEPKCJNY-UHFFFAOYSA-N 5-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-6-(3-fluoroazetidin-1-yl)pyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C#CC=1C(=NC=C(C(=O)O)C=1)N1CC(C1)F YDLTVBMEPKCJNY-UHFFFAOYSA-N 0.000 claims description 3
- RWXJVDQCJRWGRT-UHFFFAOYSA-N 5-[3-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]-2-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NOC(=N1)C=1C=CC(=C(C(=O)O)C=1)OC RWXJVDQCJRWGRT-UHFFFAOYSA-N 0.000 claims description 3
- LCCVQASEJONYNN-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2,3-dimethoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=C(C(=O)O)C=1)OC)OC LCCVQASEJONYNN-UHFFFAOYSA-N 0.000 claims description 3
- XOIYZDBLHCTKEX-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-fluoro-3-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=C(C(=O)O)C=1)F)OC XOIYZDBLHCTKEX-UHFFFAOYSA-N 0.000 claims description 3
- NLNAQGCGEJRVNM-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-methoxybenzamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=CC(=C(C(=O)N)C=1)OC NLNAQGCGEJRVNM-UHFFFAOYSA-N 0.000 claims description 3
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- 206010004664 Biliary fibrosis Diseases 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
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- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 claims 18
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
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- FWZOJLZJEACICV-UHFFFAOYSA-N 2-[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]-1-bicyclo[2.2.2]octanyl]-1,3-benzothiazole-7-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1SC(=N2)C12CCC(CC1)(CC2)C=CC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 FWZOJLZJEACICV-UHFFFAOYSA-N 0.000 claims 4
- QQCOSZYRAHCCTO-UHFFFAOYSA-N 2-[4-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]ethenyl]-1-bicyclo[2.2.2]octanyl]-1,3-benzothiazole-7-carboxylic acid Chemical compound C1CC1C2=C(C(=NO2)C3=CC=CC=C3OC(F)(F)F)C=CC45CCC(CC4)(CC5)C6=NC7=CC=CC(=C7S6)C(=O)O QQCOSZYRAHCCTO-UHFFFAOYSA-N 0.000 claims 4
- VXXJEQJGJCXXES-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-2-methoxybenzoic acid Chemical compound COC1=C(C=CC=C1C(O)=O)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 VXXJEQJGJCXXES-UHFFFAOYSA-N 0.000 claims 4
- PVGLYQXOHNMBFM-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C(=C(C(=O)O)C=CC=1)OC PVGLYQXOHNMBFM-UHFFFAOYSA-N 0.000 claims 4
- FVHPLBPMZJNGCZ-UHFFFAOYSA-N 3-[[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]bicyclo[2.2.2]octane-1-carbonyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C23CCC(CC2)(CC3)C=CC2=C(ON=C2C2=C(Cl)C=CC=C2Cl)C2CC2)=C1 FVHPLBPMZJNGCZ-UHFFFAOYSA-N 0.000 claims 4
- QNCUSMLZWUPDEV-UHFFFAOYSA-N 4-[5-[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]-1-bicyclo[2.2.1]heptanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C=CC12CCC(CC1)(C2)C1=NC(=NO1)C1=CC=C(C(=O)O)C=C1 QNCUSMLZWUPDEV-UHFFFAOYSA-N 0.000 claims 4
- YCAPXSMYWUQRGA-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-6-methoxypyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C1=CC(=NC(=C1)OC)C(=O)O YCAPXSMYWUQRGA-UHFFFAOYSA-N 0.000 claims 4
- AMOBTAXYXRZTCM-UHFFFAOYSA-N 5-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]pyrazolo[1,5-a]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=C2C=C(C=CN2N=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 AMOBTAXYXRZTCM-UHFFFAOYSA-N 0.000 claims 4
- OMMFZYRVNFAUHZ-UHFFFAOYSA-N 7-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methyl]-6,8-dihydro-5H-imidazo[1,2-a]pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN2CCN(CC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=CC=C3Cl)C3CC3)CC2=N1 OMMFZYRVNFAUHZ-UHFFFAOYSA-N 0.000 claims 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 4
- ORSZGLLQNYSMNO-UHFFFAOYSA-N 1,3-benzothiazole-7-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1SC=N2 ORSZGLLQNYSMNO-UHFFFAOYSA-N 0.000 claims 3
- MZKGPWOMKIOYOR-AATRIKPKSA-N 2-[4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-3-fluorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC(F)=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1 MZKGPWOMKIOYOR-AATRIKPKSA-N 0.000 claims 3
- YNUYDKHIIIRLKZ-UHFFFAOYSA-N 1-(azetidin-1-yl)-7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]isoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(C=C2)C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(=N1)N1CCC1 YNUYDKHIIIRLKZ-UHFFFAOYSA-N 0.000 claims 2
- UASJWEHTQXRDCF-UHFFFAOYSA-N 1-(cyclopropylamino)-7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]isoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(C=C2)C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(NC2CC2)=N1 UASJWEHTQXRDCF-UHFFFAOYSA-N 0.000 claims 2
- MIKSITSFBHXCLH-UHFFFAOYSA-N 1-[3-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-hydroxymethyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(C=1C=C(C=CC=1)C1(CC1)C(=O)O)O MIKSITSFBHXCLH-UHFFFAOYSA-N 0.000 claims 2
- OAYASYFORALBMA-UHFFFAOYSA-N 1-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]cyclopropane-1-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C1(CC1)C(=O)O OAYASYFORALBMA-UHFFFAOYSA-N 0.000 claims 2
- GIKNQEQASOSMSW-UHFFFAOYSA-N 1-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methyl]-5-(difluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)CN1N=CC(=C1C(F)F)C(=O)O GIKNQEQASOSMSW-UHFFFAOYSA-N 0.000 claims 2
- DLKATGBZWZVTLK-UHFFFAOYSA-N 1-anilino-7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]isoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(C=C2)C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(NC2=CC=CC=C2)=N1 DLKATGBZWZVTLK-UHFFFAOYSA-N 0.000 claims 2
- WTHSRRCOVIDHTL-AATRIKPKSA-N 1-chloro-7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]isoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(\C=C\C34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2)C(Cl)=N1 WTHSRRCOVIDHTL-AATRIKPKSA-N 0.000 claims 2
- COKATMFAAIHOFX-CMDGGOBGSA-N 1-cyclobutyloxy-7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]isoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(\C=C\C34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2)C(OC2CCC2)=N1 COKATMFAAIHOFX-CMDGGOBGSA-N 0.000 claims 2
- QVJYKNGWBFDKHY-MDZDMXLPSA-N 1-cyclopentyloxy-7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]isoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(\C=C\C34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2)C(OC2CCCC2)=N1 QVJYKNGWBFDKHY-MDZDMXLPSA-N 0.000 claims 2
- MBGAXGKHADNKCF-UHFFFAOYSA-N 1-cyclopropyl-5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=NN(C2CC2)C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1 MBGAXGKHADNKCF-UHFFFAOYSA-N 0.000 claims 2
- VZFHILQNKSNOBP-UHFFFAOYSA-N 2-[1-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]bicyclo[2.2.2]octane-1-carbonyl]piperidin-4-yl]acetic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(=O)N1CCC(CC1)CC(=O)O VZFHILQNKSNOBP-UHFFFAOYSA-N 0.000 claims 2
- NSSYCGXGDFDAML-UHFFFAOYSA-N 2-[2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]pyridine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C#CC=1C=C(C(=O)O)C=CN=1 NSSYCGXGDFDAML-UHFFFAOYSA-N 0.000 claims 2
- VIJZNJQUTQIPIL-UHFFFAOYSA-N 2-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C#CC=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F VIJZNJQUTQIPIL-UHFFFAOYSA-N 0.000 claims 2
- XXCHIJLFLLIORN-UHFFFAOYSA-N 2-[2-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]phenyl]acetic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=C(C=CC=C1)CC(=O)O XXCHIJLFLLIORN-UHFFFAOYSA-N 0.000 claims 2
- GMOMKEOJVFSVDE-UHFFFAOYSA-N 2-[2-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methylamino]-4-methyl-1,3-thiazol-5-yl]acetic acid Chemical compound Cc1nc(NCC23CCC(CC2)(CC3)OCc2c(onc2-c2c(Cl)cccc2Cl)C2CC2)sc1CC(O)=O GMOMKEOJVFSVDE-UHFFFAOYSA-N 0.000 claims 2
- OYYYXAPLNZADQI-VOTSOKGWSA-N 2-[3-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1 OYYYXAPLNZADQI-VOTSOKGWSA-N 0.000 claims 2
- FGCVFKBIRAIUQW-UHFFFAOYSA-N 2-[3-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]phenyl]acetic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C=CC=1)CC(=O)O FGCVFKBIRAIUQW-UHFFFAOYSA-N 0.000 claims 2
- GASIPMLUHJGRDS-UHFFFAOYSA-N 2-[3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-5-ethylpyrazol-1-yl]acetic acid Chemical compound CCC1=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=NN1CC(O)=O GASIPMLUHJGRDS-UHFFFAOYSA-N 0.000 claims 2
- LPZUOUFFLBGESV-UHFFFAOYSA-N 2-[3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methylamino]pyrazol-1-yl]acetic acid Chemical compound OC(=O)Cn1ccc(NCC23CCC(CC2)(CC3)OCc2c(onc2-c2c(Cl)cncc2Cl)C2CC2)n1 LPZUOUFFLBGESV-UHFFFAOYSA-N 0.000 claims 2
- KXMVLIDXEPLILP-AATRIKPKSA-N 2-[4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-2-fluorophenyl]acetic acid Chemical compound OC(=O)CC1=CC=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1F KXMVLIDXEPLILP-AATRIKPKSA-N 0.000 claims 2
- TWLKAAFQTSOUNU-AATRIKPKSA-N 2-[4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-3-(trifluoromethyl)phenyl]acetic acid Chemical compound OC(=O)Cc1ccc(\C=C\C23CCC(CC2)(CC3)OCc2c(onc2-c2c(Cl)cncc2Cl)C2CC2)c(c1)C(F)(F)F TWLKAAFQTSOUNU-AATRIKPKSA-N 0.000 claims 2
- MJQZKZWQWOSOOH-AATRIKPKSA-N 2-[4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-3-fluorophenyl]acetic acid Chemical compound OC(=O)CC1=CC(F)=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1 MJQZKZWQWOSOOH-AATRIKPKSA-N 0.000 claims 2
- JMHHCBCASLRABU-BQYQJAHWSA-N 2-[4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]phenyl]-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(=N1)C1=CC=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1 JMHHCBCASLRABU-BQYQJAHWSA-N 0.000 claims 2
- PIYJSXJPHLJSDL-MDZDMXLPSA-N 2-[4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]phenyl]-N,N-dimethylacetamide Chemical compound CN(C)C(=O)CC1=CC=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1 PIYJSXJPHLJSDL-MDZDMXLPSA-N 0.000 claims 2
- MORPYGNWNGUWCK-CMDGGOBGSA-N 2-[4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]phenyl]-N-methylacetamide Chemical compound CNC(=O)CC1=CC=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1 MORPYGNWNGUWCK-CMDGGOBGSA-N 0.000 claims 2
- XFLKGOONVOYBFA-HWKANZROSA-N 2-[4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]pyridin-2-yl]oxyacetic acid Chemical compound OC(=O)COC1=NC=CC(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1 XFLKGOONVOYBFA-HWKANZROSA-N 0.000 claims 2
- AFIOBOUXPNRWNF-UHFFFAOYSA-N 2-[4-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-2-fluorophenyl]acetic acid Chemical compound OC(=O)CC1=CC=C(C=C1F)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 AFIOBOUXPNRWNF-UHFFFAOYSA-N 0.000 claims 2
- SIGZLXFDGVPTJK-UHFFFAOYSA-N 2-[4-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-3-(trifluoromethyl)phenyl]acetic acid Chemical compound OC(=O)Cc1ccc(C#CC23CCC(CC2)(CC3)OCc2c(onc2-c2c(Cl)cncc2Cl)C2CC2)c(c1)C(F)(F)F SIGZLXFDGVPTJK-UHFFFAOYSA-N 0.000 claims 2
- KZXVHNOKQURXGC-UHFFFAOYSA-N 2-[4-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-3-fluorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(F)=C1 KZXVHNOKQURXGC-UHFFFAOYSA-N 0.000 claims 2
- IVTUQNIKNGOFTD-UHFFFAOYSA-N 2-[4-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]pyridin-2-yl]oxyacetic acid Chemical compound OC(=O)COC1=NC=CC(=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 IVTUQNIKNGOFTD-UHFFFAOYSA-N 0.000 claims 2
- LYEIIEQYNIJWFN-UHFFFAOYSA-N 2-[4-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]ethyl]-1-bicyclo[2.2.2]octanyl]-1,3-benzothiazole-7-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)CCC12CCC(CC1)(CC2)C=1SC2=C(N=1)C=CC=C2C(=O)O LYEIIEQYNIJWFN-UHFFFAOYSA-N 0.000 claims 2
- SJQJDPIBWCASQW-UHFFFAOYSA-N 2-[4-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]phenoxy]propanoic acid Chemical compound CC(OC1=CC=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1)C(O)=O SJQJDPIBWCASQW-UHFFFAOYSA-N 0.000 claims 2
- FNMVSJWDWYCICG-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,2-difluoro-1-methylcyclopropyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]quinoline-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1(C(C1)(F)F)C)COC12CCC(CC1)(CC2)C1=NC=2C=CC=C(C=2C=C1)C(=O)O FNMVSJWDWYCICG-UHFFFAOYSA-N 0.000 claims 2
- GRWMHEKFBZLRJM-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,3-benzothiazole-6-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C1)N=C(S2)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 GRWMHEKFBZLRJM-UHFFFAOYSA-N 0.000 claims 2
- CFLWZKKOSLLPFS-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]pyridine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1C=C(C(=O)O)C=CN=1 CFLWZKKOSLLPFS-UHFFFAOYSA-N 0.000 claims 2
- VDWVQQGOPBOGRE-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]quinazoline-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC2=CC=C(C=C2C=N1)C(=O)O VDWVQQGOPBOGRE-UHFFFAOYSA-N 0.000 claims 2
- WGPXBGGTZUUQQC-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]quinoline-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC2=CC=C(C=C2C=C1)C(=O)O WGPXBGGTZUUQQC-UHFFFAOYSA-N 0.000 claims 2
- VJSAXAGDGVUHLQ-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-2-oxabicyclo[2.2.2]octan-1-yl]-1,3-benzothiazole-7-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12COC(CC1)(CC2)C=1SC2=C(N=1)C=CC=C2C(=O)O VJSAXAGDGVUHLQ-UHFFFAOYSA-N 0.000 claims 2
- GXWUJQPIBXQGMQ-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]bicyclo[2.2.2]octane-1-carbonyl]-3,4-dihydro-1H-isoquinoline-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(=O)N1CC=2C=CC=C(C=2CC1)C(=O)O GXWUJQPIBXQGMQ-UHFFFAOYSA-N 0.000 claims 2
- WLLQLLQIMFKEHZ-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]bicyclo[2.2.2]octane-1-carbonyl]-3,4-dihydro-1H-isoquinoline-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(=O)N1CC2=CC=C(C=C2CC1)C(=O)O WLLQLLQIMFKEHZ-UHFFFAOYSA-N 0.000 claims 2
- ZBRXAPRGIYZWBP-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]bicyclo[2.2.2]octane-1-carbonyl]-3,4-dihydro-1H-isoquinoline-8-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(=O)N1CC2=C(C=CC=C2CC1)C(=O)O ZBRXAPRGIYZWBP-UHFFFAOYSA-N 0.000 claims 2
- UGALHDBBHDUBMX-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12CCC(CC1)(CC2)C=1SC2=C(N=1)C=CC(=C2)C(=O)O UGALHDBBHDUBMX-UHFFFAOYSA-N 0.000 claims 2
- ZSSCUJNLDKCRQQ-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,3-benzoxazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12CCC(CC1)(CC2)C=1OC2=C(N=1)C=CC(=C2)C(=O)O ZSSCUJNLDKCRQQ-UHFFFAOYSA-N 0.000 claims 2
- PNYIICMNDMXEGB-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,3-thiazole-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12CCC(CC1)(CC2)C=1SC=C(N=1)C(=O)O PNYIICMNDMXEGB-UHFFFAOYSA-N 0.000 claims 2
- CYCLZAVSVDDBDM-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12CCC(CC1)(CC2)C=1SC(=C(N=1)C)C(=O)O CYCLZAVSVDDBDM-UHFFFAOYSA-N 0.000 claims 2
- YXVSTHAINMSHLT-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(=N1)C12CCC(COCC3=C(ON=C3C3=C(Cl)C=CC=C3Cl)C3CC3)(CC1)CO2 YXVSTHAINMSHLT-UHFFFAOYSA-N 0.000 claims 2
- SKARHFXXQRDVED-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,3-benzothiazole-7-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1SC2=C(N=1)C=CC=C2C(=O)O SKARHFXXQRDVED-UHFFFAOYSA-N 0.000 claims 2
- DIOMJYZUMUEJOD-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F DIOMJYZUMUEJOD-UHFFFAOYSA-N 0.000 claims 2
- XKJVRZKELVRCDG-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-5-(trifluoromethyl)-1,3-benzothiazole-7-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1SC2=C(N=1)C=C(C=C2C(=O)O)C(F)(F)F XKJVRZKELVRCDG-UHFFFAOYSA-N 0.000 claims 2
- BGRBSSFDFYXYPH-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-5-(trifluoromethyl)quinoline-7-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=CC(=N2)C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(=C1)C(F)(F)F BGRBSSFDFYXYPH-UHFFFAOYSA-N 0.000 claims 2
- DXUBXDHUOMYKBZ-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-6-fluoro-1,3-benzothiazole-7-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1SC2=C(N=1)C=CC(=C2C(=O)O)F DXUBXDHUOMYKBZ-UHFFFAOYSA-N 0.000 claims 2
- VZLGSTKSUYAQNZ-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-6-methoxyquinoline-5-carboxylic acid Chemical compound COC1=C(C(O)=O)C2=C(C=C1)N=C(C=C2)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 VZLGSTKSUYAQNZ-UHFFFAOYSA-N 0.000 claims 2
- WZDQHEVIWLCSLF-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-7-(trifluoromethyl)quinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC(=CC2=C1C=CC(=N2)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(F)(F)F WZDQHEVIWLCSLF-UHFFFAOYSA-N 0.000 claims 2
- FKBKIWNUCUBWAN-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-(2-hydroxy-2-methylpropoxy)quinoline-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC=2C(=CC=C(C=2C=C1)C(=O)O)OCC(C)(C)O FKBKIWNUCUBWAN-UHFFFAOYSA-N 0.000 claims 2
- KUDDWIOSXRMZPP-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-(3-methoxypropoxy)quinoline-6-carboxylic acid Chemical compound COCCCOC1=CC(=CC2=C1N=C(C=C2)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O KUDDWIOSXRMZPP-UHFFFAOYSA-N 0.000 claims 2
- ISQFLTCJDFBHHA-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-(4-methylpiperazin-1-yl)quinoline-5-carboxylic acid Chemical compound CN1CCN(CC1)C1=CC=C(C(O)=O)C2=CC=C(N=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 ISQFLTCJDFBHHA-UHFFFAOYSA-N 0.000 claims 2
- YULOLRRJARARHD-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-(cyclopropylmethoxy)quinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC=C(OCC2CC2)C2=NC(=CC=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 YULOLRRJARARHD-UHFFFAOYSA-N 0.000 claims 2
- MTNUKQZXOCAOIR-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-(oxan-4-yloxy)quinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC=C(OC2CCOCC2)C2=NC(=CC=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 MTNUKQZXOCAOIR-UHFFFAOYSA-N 0.000 claims 2
- AXJWXWHTELKSOZ-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-(oxetan-3-yloxy)quinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC=C(OC2COC2)C2=NC(=CC=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 AXJWXWHTELKSOZ-UHFFFAOYSA-N 0.000 claims 2
- FHBSBBXQLLGBBP-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-(oxetan-3-yloxy)quinoline-6-carboxylic acid Chemical compound OC(=O)C1=CC2=C(N=C(C=C2)C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(OC2COC2)=C1 FHBSBBXQLLGBBP-UHFFFAOYSA-N 0.000 claims 2
- MEPPIPGTOKSMRR-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-(oxolan-3-yloxy)quinoline-6-carboxylic acid Chemical compound OC(=O)C1=CC2=C(N=C(C=C2)C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(OC2CCOC2)=C1 MEPPIPGTOKSMRR-UHFFFAOYSA-N 0.000 claims 2
- OIRVTLYUXMHOIV-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-(trifluoromethyl)quinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC=C(C2=NC(=CC=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(F)(F)F OIRVTLYUXMHOIV-UHFFFAOYSA-N 0.000 claims 2
- PGZFNBBQFNMPQR-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-(trifluoromethyl)quinoline-6-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=C(N=C2C(=C1)C(F)(F)F)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 PGZFNBBQFNMPQR-UHFFFAOYSA-N 0.000 claims 2
- WPYWIOPLTFLQGN-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-fluoroquinoline-6-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=C(N=C2C(F)=C1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 WPYWIOPLTFLQGN-UHFFFAOYSA-N 0.000 claims 2
- SIRVQDTVVSUCLG-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-hydroxyquinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC=C(O)C2=NC(=CC=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 SIRVQDTVVSUCLG-UHFFFAOYSA-N 0.000 claims 2
- OXVJUKFVDFFXMA-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-methoxyquinoline-5-carboxylic acid Chemical compound COC1=CC=C(C(O)=O)C2=CC=C(N=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 OXVJUKFVDFFXMA-UHFFFAOYSA-N 0.000 claims 2
- OOMFPJKYLUBFCO-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-methylquinoline-5-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C2=CC=C(N=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 OOMFPJKYLUBFCO-UHFFFAOYSA-N 0.000 claims 2
- FLZAXVLXEIAVEY-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-morpholin-4-ylquinoline-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC=2C(=CC=C(C=2C=C1)C(=O)O)N1CCOCC1 FLZAXVLXEIAVEY-UHFFFAOYSA-N 0.000 claims 2
- GQZQHOANKCWOCK-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-morpholin-4-ylquinoline-6-carboxylic acid Chemical compound OC(=O)C1=CC2=C(N=C(C=C2)C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(=C1)N1CCOCC1 GQZQHOANKCWOCK-UHFFFAOYSA-N 0.000 claims 2
- PMEZLPBEMUVZTI-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-propan-2-yloxyquinoline-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC=2C(=CC=C(C=2C=C1)C(=O)O)OC(C)C PMEZLPBEMUVZTI-UHFFFAOYSA-N 0.000 claims 2
- WAMGLBALJXEOHI-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-pyrrolidin-1-ylquinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC=C(N2CCCC2)C2=NC(=CC=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 WAMGLBALJXEOHI-UHFFFAOYSA-N 0.000 claims 2
- UDSKFKJXXCUHST-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]quinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=NC(=CC=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 UDSKFKJXXCUHST-UHFFFAOYSA-N 0.000 claims 2
- FOYMVMLVLIIZOS-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-(dicyclopropylmethyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-7-(trifluoromethyl)quinoline-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C(C1CC1)C1CC1)COC12CCC(CC1)(CC2)C1=NC=2C=C(C=C(C=2C=C1)C(=O)O)C(F)(F)F FOYMVMLVLIIZOS-UHFFFAOYSA-N 0.000 claims 2
- BSHYILBOKGIEIN-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,3-benzothiazole-6-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C1)N=C(S2)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1OC(F)(F)F)C1CC1 BSHYILBOKGIEIN-UHFFFAOYSA-N 0.000 claims 2
- XMRUTTLFGJEBEM-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)COC12CCC(CC1)(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F XMRUTTLFGJEBEM-UHFFFAOYSA-N 0.000 claims 2
- QMYDZSITTJBTTH-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]quinazoline-6-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C1)N=C(N=C2)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1OC(F)(F)F)C1CC1 QMYDZSITTJBTTH-UHFFFAOYSA-N 0.000 claims 2
- ZNYYFNOKZWCJII-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(=N1)C12CCC(COCC3=C(ON=C3C3=C(OC(F)(F)F)C=CC=C3)C3CC3)(CC1)CO2 ZNYYFNOKZWCJII-UHFFFAOYSA-N 0.000 claims 2
- UBJLWZIZLGZQPR-UHFFFAOYSA-N 2-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound OC(=O)C1=CC2=C(N=C(S2)C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=CC=CC=C2C(F)(F)F)C2CC2)C(F)=C1 UBJLWZIZLGZQPR-UHFFFAOYSA-N 0.000 claims 2
- CLJMUWUBOGWZGS-AATRIKPKSA-N 2-[5-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]pyridin-2-yl]acetic acid Chemical compound OC(=O)CC1=CC=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=N1 CLJMUWUBOGWZGS-AATRIKPKSA-N 0.000 claims 2
- DLRBUARSOFLKGN-AATRIKPKSA-N 2-[5-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]pyridin-2-yl]oxyacetic acid Chemical compound OC(=O)COC1=CC=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=N1 DLRBUARSOFLKGN-AATRIKPKSA-N 0.000 claims 2
- QVGDSDQMNKCFLT-UHFFFAOYSA-N 2-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]cyclopropane-1-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C1C(C1)C(=O)O QVGDSDQMNKCFLT-UHFFFAOYSA-N 0.000 claims 2
- NAXDZGAMYZVHKL-UHFFFAOYSA-N 2-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CN=1 NAXDZGAMYZVHKL-UHFFFAOYSA-N 0.000 claims 2
- MTBVJYHELGSHOV-UHFFFAOYSA-N 2-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]cyclopropane-1-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C1C(C1)C(=O)O MTBVJYHELGSHOV-UHFFFAOYSA-N 0.000 claims 2
- ALUZIFDFSMWCNQ-BQYQJAHWSA-N 2-[[4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]phenyl]methoxy]acetic acid Chemical compound OC(=O)COCC1=CC=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1 ALUZIFDFSMWCNQ-BQYQJAHWSA-N 0.000 claims 2
- NZNFNUOIGFQZFF-UHFFFAOYSA-N 2-[[4-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]phenyl]methoxy]acetic acid Chemical compound OC(=O)COCC1=CC=C(C=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 NZNFNUOIGFQZFF-UHFFFAOYSA-N 0.000 claims 2
- BLIHJPCDANQCPJ-UHFFFAOYSA-N 2-[[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]-1-bicyclo[2.2.2]octanyl]methoxy]-1,3-benzothiazole-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=C(OCC34CCC(CC3)(CC4)C=CC3=C(ON=C3C3=C(Cl)C=CC=C3Cl)C3CC3)SC2=C1 BLIHJPCDANQCPJ-UHFFFAOYSA-N 0.000 claims 2
- QYDJRIBEWYNZSD-UHFFFAOYSA-N 2-[[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]-1-bicyclo[2.2.2]octanyl]methoxy]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound OC(=O)C1=CC(F)=C2N=C(OCC34CCC(CC3)(CC4)C=CC3=C(ON=C3C3=C(Cl)C=CC=C3Cl)C3CC3)SC2=C1 QYDJRIBEWYNZSD-UHFFFAOYSA-N 0.000 claims 2
- APCNPQASXSVHHU-UHFFFAOYSA-N 2-[[4-[[3-(3-chloro-5-methoxypyridin-4-yl)-5-cyclopropyl-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-methoxyquinoline-6-carboxylic acid Chemical compound ClC=1C=NC=C(C=1C1=NOC(=C1COC12CCC(CC1)(CC2)COC1=NC2=CC=C(C=C2C(=C1)OC)C(=O)O)C1CC1)OC APCNPQASXSVHHU-UHFFFAOYSA-N 0.000 claims 2
- BIBKQUNGQCLUJX-UHFFFAOYSA-N 2-[[4-[[3-(3-chloro-5-methoxypyridin-4-yl)-5-cyclopropyl-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-8-cyclopropylquinoline-6-carboxylic acid Chemical compound ClC=1C=NC=C(C=1C1=NOC(=C1COC12CCC(CC1)(CC2)COC1=NC2=C(C=C(C=C2C=C1)C(=O)O)C1CC1)C1CC1)OC BIBKQUNGQCLUJX-UHFFFAOYSA-N 0.000 claims 2
- BJAUQRZOTFDMFP-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-hydroxymethyl]-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(C=1SC2=C(N=1)C=CC(=C2)C(=O)O)O BJAUQRZOTFDMFP-UHFFFAOYSA-N 0.000 claims 2
- RRMNLDUMZOJPHY-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-hydroxymethyl]-4-fluoro-1,3-benzothiazole-6-carboxamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(C=1SC2=C(N=1)C(=CC(=C2)C(=O)N)F)O RRMNLDUMZOJPHY-UHFFFAOYSA-N 0.000 claims 2
- XZPJFFTVOYYYDS-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyridine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=O)O)C=CN=1 XZPJFFTVOYYYDS-UHFFFAOYSA-N 0.000 claims 2
- AKARZHRKWSJNCE-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyrimidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=NC=CC(=N1)C(=O)O AKARZHRKWSJNCE-UHFFFAOYSA-N 0.000 claims 2
- LQWJTXSONPLUMD-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methyl]-3,4-dihydro-1H-isoquinoline-7-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)CN1CC2=CC(=CC=C2CC1)C(=O)O LQWJTXSONPLUMD-UHFFFAOYSA-N 0.000 claims 2
- DFWMAUFKEPCZOJ-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-1,3-thiazole-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1SC=C(N=1)C(=O)O DFWMAUFKEPCZOJ-UHFFFAOYSA-N 0.000 claims 2
- SSEYHKOQIGHGPR-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C1=C(N=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)S1)C(F)(F)F SSEYHKOQIGHGPR-UHFFFAOYSA-N 0.000 claims 2
- VDJQPWHDAUTVIX-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC1=C(SC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=N1)C(O)=O VDJQPWHDAUTVIX-UHFFFAOYSA-N 0.000 claims 2
- JUCFVLHGIBHNEX-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-5-fluoro-1,3-benzothiazole-7-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1SC2=C(N=1)C=C(C=C2C(=O)O)F JUCFVLHGIBHNEX-UHFFFAOYSA-N 0.000 claims 2
- HYFNLAKDEHXKCP-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-8-methoxyquinoline-5-carboxylic acid Chemical compound COC1=CC=C(C(O)=O)C2=C1N=C(OCC13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2 HYFNLAKDEHXKCP-UHFFFAOYSA-N 0.000 claims 2
- YLRPVGNOQAKVMP-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-8-methoxyquinoline-6-carboxylic acid Chemical compound COC1=CC(=CC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)N=C12)C(O)=O YLRPVGNOQAKVMP-UHFFFAOYSA-N 0.000 claims 2
- FVVZROMHBWABBO-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]imidazo[1,2-a]pyridine-7-carboxylic acid Chemical compound OC(=O)C1=CC2=NC(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)=CN2C=C1 FVVZROMHBWABBO-UHFFFAOYSA-N 0.000 claims 2
- HMGRJAXOGQJXPW-UHFFFAOYSA-N 2-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]quinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1C=CC(OCC13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)=N2 HMGRJAXOGQJXPW-UHFFFAOYSA-N 0.000 claims 2
- PLHOKKPKPZKPEH-UHFFFAOYSA-N 2-[[5-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]pyridin-2-yl]methoxy]acetic acid Chemical compound OC(=O)COCC1=CC=C(C=N1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 PLHOKKPKPZKPEH-UHFFFAOYSA-N 0.000 claims 2
- ARGJZKHOYUFENQ-UHFFFAOYSA-N 2-[[6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]pyridin-3-yl]methoxy]acetic acid Chemical compound OC(=O)COCC1=CC=C(N=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 ARGJZKHOYUFENQ-UHFFFAOYSA-N 0.000 claims 2
- BBABMYPSSZSIBI-UHFFFAOYSA-N 2-[[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]bicyclo[2.2.2]octane-1-carbonyl]-methylamino]methyl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(=O)N(C)CC1=C(C(=O)O)C=CC=C1 BBABMYPSSZSIBI-UHFFFAOYSA-N 0.000 claims 2
- TYOXRISAXXIVAF-UHFFFAOYSA-N 2-[[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]bicyclo[2.2.2]octane-1-carbonyl]amino]methyl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(=O)NCC1=C(C(=O)O)C=CC=C1 TYOXRISAXXIVAF-UHFFFAOYSA-N 0.000 claims 2
- RQRIGFGPOOOHHM-UHFFFAOYSA-N 2-chloro-3-[[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]bicyclo[2.2.2]octane-1-carbonyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C23CCC(CC2)(CC3)C=CC2=C(ON=C2C2=C(Cl)C=CC=C2Cl)C2CC2)=C1Cl RQRIGFGPOOOHHM-UHFFFAOYSA-N 0.000 claims 2
- QHILBULUBUBURK-UHFFFAOYSA-N 2-chloro-3-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]bicyclo[2.2.2]octane-1-carbonyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C23CCC(COCC4=C(ON=C4C4=C(Cl)C=CC=C4Cl)C4CC4)(CC2)CC3)=C1Cl QHILBULUBUBURK-UHFFFAOYSA-N 0.000 claims 2
- DMTLWRBTDNMMPU-UHFFFAOYSA-N 2-cyclopropyl-5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=NN1C1CC1 DMTLWRBTDNMMPU-UHFFFAOYSA-N 0.000 claims 2
- TUHGQIBMTUQNRU-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-2-hydroxyethyl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(CC=1C=C(C(=O)O)C=CC=1)O TUHGQIBMTUQNRU-UHFFFAOYSA-N 0.000 claims 2
- NQMFSFLXPUEVTD-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-methylindole-6-carboxylic acid Chemical compound CN1C=C(C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C2=CC=C(C=C12)C(O)=O NQMFSFLXPUEVTD-UHFFFAOYSA-N 0.000 claims 2
- WKCWRPFFAKBFQJ-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-5-(methoxymethyl)benzoic acid Chemical compound COCC1=CC(=CC(=C1)C(O)=O)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 WKCWRPFFAKBFQJ-UHFFFAOYSA-N 0.000 claims 2
- ABDUJJAYDHOSBU-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-5-(trifluoromethoxy)benzoic acid Chemical compound OC(=O)C1=CC(OC(F)(F)F)=CC(=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 ABDUJJAYDHOSBU-UHFFFAOYSA-N 0.000 claims 2
- PTHUMIAEZRHECP-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-5-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(=CC(=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(F)(F)F PTHUMIAEZRHECP-UHFFFAOYSA-N 0.000 claims 2
- MIFSNPMXFRVBMY-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-5-methoxybenzoic acid Chemical compound COC1=CC(=CC(=C1)C(O)=O)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 MIFSNPMXFRVBMY-UHFFFAOYSA-N 0.000 claims 2
- UHLIVNBWVKYELG-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-5-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC(=CC(=C1)C(O)=O)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 UHLIVNBWVKYELG-UHFFFAOYSA-N 0.000 claims 2
- PZINQWGJMRPHLK-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-8-carboxylic acid Chemical compound OC(=O)c1cc(cn2c(cnc12)C#CC12CCC(CC1)(CC2)OCc1c(onc1-c1c(Cl)cncc1Cl)C1CC1)C(F)(F)F PZINQWGJMRPHLK-UHFFFAOYSA-N 0.000 claims 2
- CTQGXEMFWKWLOG-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-6-ethylimidazo[1,2-a]pyridine-8-carboxylic acid Chemical compound CCC1=CN2C(=CN=C2C(=C1)C(O)=O)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 CTQGXEMFWKWLOG-UHFFFAOYSA-N 0.000 claims 2
- HTHOEVYGLIKVHB-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]imidazo[1,2-a]pyridine-7-carboxylic acid Chemical compound OC(=O)C1=CC2=NC=C(C#CC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)N2C=C1 HTHOEVYGLIKVHB-UHFFFAOYSA-N 0.000 claims 2
- MAAOAVJEYBCDTN-UHFFFAOYSA-N 3-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]imidazo[1,2-a]pyridine-8-carboxylic acid Chemical compound OC(=O)C1=CC=CN2C(=CN=C12)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 MAAOAVJEYBCDTN-UHFFFAOYSA-N 0.000 claims 2
- KOEWDFJNXGFEPL-CMDGGOBGSA-N 3-[3-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=CC(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1 KOEWDFJNXGFEPL-CMDGGOBGSA-N 0.000 claims 2
- VMFAKWFEPOEJNC-UHFFFAOYSA-N 3-[3-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(=C1)C1=NC(=NO1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 VMFAKWFEPOEJNC-UHFFFAOYSA-N 0.000 claims 2
- OFRLZPLBXIKXMQ-UHFFFAOYSA-N 3-[3-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(=C1)C1=NC(=NO1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1OC(F)(F)F)C1CC1 OFRLZPLBXIKXMQ-UHFFFAOYSA-N 0.000 claims 2
- BFWJNSGEBQVPJR-UHFFFAOYSA-N 3-[3-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)C(F)(F)F)COC12CCC(CC1)(CC2)C1=NOC(=N1)C=1C=C(C(=O)O)C=CC=1 BFWJNSGEBQVPJR-UHFFFAOYSA-N 0.000 claims 2
- BXWKZOMMLRAZKI-BQYQJAHWSA-N 3-[4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-2-fluorophenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1F BXWKZOMMLRAZKI-BQYQJAHWSA-N 0.000 claims 2
- LLTLKVNZUINLLD-UHFFFAOYSA-N 3-[4-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=C(C=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 LLTLKVNZUINLLD-UHFFFAOYSA-N 0.000 claims 2
- KBTKDNSGMFQSJN-UHFFFAOYSA-N 3-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]-N-methylsulfonylbenzamide Chemical compound CS(=O)(=O)NC(=O)C1=CC=CC(=C1)C12CCC(COCC3=C(ON=C3C3=C(Cl)C=CC=C3Cl)C3CC3)(CC1)CO2 KBTKDNSGMFQSJN-UHFFFAOYSA-N 0.000 claims 2
- LADYWUOKVAOOOU-UHFFFAOYSA-N 3-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12COC(CC1)(CC2)C=1C=C(C(=O)O)C=CC=1 LADYWUOKVAOOOU-UHFFFAOYSA-N 0.000 claims 2
- YVMWKSJWOQVWOA-UHFFFAOYSA-N 3-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]-5-(trifluoromethyl)benzamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COCC12COC(CC1)(CC2)C=1C=C(C(=O)N)C=C(C=1)C(F)(F)F YVMWKSJWOQVWOA-UHFFFAOYSA-N 0.000 claims 2
- WHVBWQWYTWCBEJ-UHFFFAOYSA-N 3-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]-5-(trifluoromethyl)benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COCC12COC(CC1)(CC2)C=1C=C(C(=O)O)C=C(C=1)C(F)(F)F WHVBWQWYTWCBEJ-UHFFFAOYSA-N 0.000 claims 2
- WIPJOIYNJSLXMU-UHFFFAOYSA-N 3-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]-5-(trifluoromethyl)benzonitrile Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COCC12COC(CC1)(CC2)C=1C=C(C#N)C=C(C=1)C(F)(F)F WIPJOIYNJSLXMU-UHFFFAOYSA-N 0.000 claims 2
- BONYTGCCCNCUJZ-UHFFFAOYSA-N 3-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COCC12COC(CC1)(CC2)C=1C=C(C(=O)O)C=CC=1 BONYTGCCCNCUJZ-UHFFFAOYSA-N 0.000 claims 2
- ONZMWFFNQYDXJQ-UHFFFAOYSA-N 3-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]benzoic acid Chemical compound OC(=O)c1cccc(c1)C12CCC(COCc3c(onc3-c3ccccc3OC(F)(F)F)C3CC3)(CC1)CO2 ONZMWFFNQYDXJQ-UHFFFAOYSA-N 0.000 claims 2
- XXFYVQVCAJTJGU-BQYQJAHWSA-N 3-[5-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-2-(2,2-difluoroethoxy)phenyl]propanoic acid Chemical compound OC(=O)CCC1=C(OCC(F)F)C=CC(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1 XXFYVQVCAJTJGU-BQYQJAHWSA-N 0.000 claims 2
- FDIVVUVFFKKSSI-CMDGGOBGSA-N 3-[5-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-2-methoxyphenyl]propanoic acid Chemical compound COC1=C(CCC(O)=O)C=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1 FDIVVUVFFKKSSI-CMDGGOBGSA-N 0.000 claims 2
- HXULRUBKXIGJRK-UHFFFAOYSA-N 3-[5-[3-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[1.1.1]pentanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12CC(C1)(C2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1 HXULRUBKXIGJRK-UHFFFAOYSA-N 0.000 claims 2
- VFLGTLCZFLXKHK-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 VFLGTLCZFLXKHK-UHFFFAOYSA-N 0.000 claims 2
- BWOXSMAZSDLVLL-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,3,4-oxadiazol-2-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(=C1)C1=NN=C(O1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 BWOXSMAZSDLVLL-UHFFFAOYSA-N 0.000 claims 2
- NADGBATYYSICMD-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,3,4-thiadiazol-2-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(=C1)C1=NN=C(S1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 NADGBATYYSICMD-UHFFFAOYSA-N 0.000 claims 2
- STNYJQLDNCURKZ-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-2-oxabicyclo[2.2.2]octan-1-yl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12COC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1 STNYJQLDNCURKZ-UHFFFAOYSA-N 0.000 claims 2
- OJDZFOAVUNYLCO-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]cuban-1-yl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12C3C4C5(C(C14)C2C53)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1 OJDZFOAVUNYLCO-UHFFFAOYSA-N 0.000 claims 2
- JCMOMIMABYTFMJ-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)triazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(N=NN1C1=C(Cl)C=CC=C1Cl)C1CC1 JCMOMIMABYTFMJ-UHFFFAOYSA-N 0.000 claims 2
- GFCMFCLCFCZIBJ-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2,5-dimethoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C(=C(C(=O)O)C=C(C=1)OC)OC GFCMFCLCFCZIBJ-UHFFFAOYSA-N 0.000 claims 2
- LIQADTAOIWSMRQ-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2,6-difluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C(=C(C(=O)O)C(=CC=1)F)F LIQADTAOIWSMRQ-UHFFFAOYSA-N 0.000 claims 2
- KMTRQYIVCJCUDB-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-fluoro-5-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C(=C(C(=O)O)C=C(C=1)OC)F KMTRQYIVCJCUDB-UHFFFAOYSA-N 0.000 claims 2
- XSBQAINLOLSXCK-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-fluoro-6-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C(=C(C(=O)O)C(=CC=1)OC)F XSBQAINLOLSXCK-UHFFFAOYSA-N 0.000 claims 2
- ZSVDAFBKKBTVNK-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C(=C(C(=O)O)C=CC=1)F ZSVDAFBKKBTVNK-UHFFFAOYSA-N 0.000 claims 2
- BZODDLTWRLDJFC-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-4-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1F BZODDLTWRLDJFC-UHFFFAOYSA-N 0.000 claims 2
- AZXOSCPIMLOMEF-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-4-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1OC AZXOSCPIMLOMEF-UHFFFAOYSA-N 0.000 claims 2
- SQJSAFXWLCRMII-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-5-(trifluoromethyl)benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=C(C=1)C(F)(F)F SQJSAFXWLCRMII-UHFFFAOYSA-N 0.000 claims 2
- URSGZIHPVYJOGW-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-5-fluoro-2-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C(=C(C(=O)O)C=C(C=1)F)OC URSGZIHPVYJOGW-UHFFFAOYSA-N 0.000 claims 2
- IWHOFALWOUHSFZ-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-5-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=C(C=1)F IWHOFALWOUHSFZ-UHFFFAOYSA-N 0.000 claims 2
- DROAEAYQUOSWBU-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-5-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=C(C=1)OC DROAEAYQUOSWBU-UHFFFAOYSA-N 0.000 claims 2
- ZNYPZGSPXJORTF-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-5-propan-2-yloxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=C(C=1)OC(C)C ZNYPZGSPXJORTF-UHFFFAOYSA-N 0.000 claims 2
- HFVDBDMXBCHOML-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1 HFVDBDMXBCHOML-UHFFFAOYSA-N 0.000 claims 2
- SKGHKCOLDJYBOG-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-2-oxabicyclo[2.2.2]octan-1-yl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(=C1)C1=NOC(=N1)C12CCC(CC1)(CO2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 SKGHKCOLDJYBOG-UHFFFAOYSA-N 0.000 claims 2
- NLWIZKXHMCCCIF-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-4-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COCC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1F NLWIZKXHMCCCIF-UHFFFAOYSA-N 0.000 claims 2
- NPJLZPMCBSKGOG-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-4-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COCC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1OC NPJLZPMCBSKGOG-UHFFFAOYSA-N 0.000 claims 2
- ANMWGNOVKKRRFP-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-5-(trifluoromethyl)benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COCC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=C(C=1)C(F)(F)F ANMWGNOVKKRRFP-UHFFFAOYSA-N 0.000 claims 2
- KJTHTTUKYWWIQM-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-(3-fluoropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1)F)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)O)C=CC=1 KJTHTTUKYWWIQM-UHFFFAOYSA-N 0.000 claims 2
- PXVJVPSOOURVKX-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,3,4-oxadiazol-2-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)COC12CCC(CC1)(CC2)C1=NN=C(O1)C=1C=C(C(=O)O)C=CC=1 PXVJVPSOOURVKX-UHFFFAOYSA-N 0.000 claims 2
- HJHBACFCTKJTOW-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,3,4-thiadiazol-2-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)COC12CCC(CC1)(CC2)C1=NN=C(S1)C=1C=C(C(=O)O)C=CC=1 HJHBACFCTKJTOW-UHFFFAOYSA-N 0.000 claims 2
- LBBDHXMSNKMXDO-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-2-oxabicyclo[2.2.2]octan-1-yl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)c1cccc(c1)-c1noc(n1)C12CCC(CC1)(CO2)OCc1c(onc1-c1ccccc1OC(F)(F)F)C1CC1 LBBDHXMSNKMXDO-UHFFFAOYSA-N 0.000 claims 2
- XNZYEKZZXTWURN-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(=C1)C1=NOC(=N1)C12CCC(COCC3=C(ON=C3C3=CC=CC=C3OC(F)(F)F)C3CC3)(CC1)CC2 XNZYEKZZXTWURN-UHFFFAOYSA-N 0.000 claims 2
- OXRWPZWNYCYSBJ-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC(=CC=C1)C1=NOC(=N1)C12CCC(COCC3=C(ON=C3C3=C(OC(F)(F)F)C=CC=C3)C3CC3)(CC1)CO2 OXRWPZWNYCYSBJ-UHFFFAOYSA-N 0.000 claims 2
- YGCYIHIJUANYDQ-UHFFFAOYSA-N 3-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1C(F)(F)F)C1CC1 YGCYIHIJUANYDQ-UHFFFAOYSA-N 0.000 claims 2
- GQQMUHQCHSPPLF-UHFFFAOYSA-N 3-[[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]bicyclo[2.2.1]heptane-1-carbonyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C23CCC(CC2)(C3)C=CC2=C(ON=C2C2=C(Cl)C=CC=C2Cl)C2CC2)=C1 GQQMUHQCHSPPLF-UHFFFAOYSA-N 0.000 claims 2
- LYUQTVQFXODQEH-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-hydroxymethyl]-4-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(C=1C=C(C(=O)O)C=CC=1F)O LYUQTVQFXODQEH-UHFFFAOYSA-N 0.000 claims 2
- FXBUHUFGIZNKAY-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C(=C(C(=O)O)C=CC=1)F FXBUHUFGIZNKAY-UHFFFAOYSA-N 0.000 claims 2
- SVXNWHRRXDBJAY-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-methylbenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C(=C(C(=O)O)C=CC=1)C SVXNWHRRXDBJAY-UHFFFAOYSA-N 0.000 claims 2
- GDCAJVAYZJYLTR-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=O)O)C=CC=1F GDCAJVAYZJYLTR-UHFFFAOYSA-N 0.000 claims 2
- UOTYJVXOVGITDR-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-5-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=O)O)C=C(C=1)F UOTYJVXOVGITDR-UHFFFAOYSA-N 0.000 claims 2
- QWCKCBLCIJXSPP-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=O)O)C=CC=1 QWCKCBLCIJXSPP-UHFFFAOYSA-N 0.000 claims 2
- BWCRCWHVDZGJSG-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]benzonitrile Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C#N)C=CC=1 BWCRCWHVDZGJSG-UHFFFAOYSA-N 0.000 claims 2
- KRFRLPRRZHLQDL-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]methoxy]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12CCC(CC1)(CC2)COC=1C=C(C(=O)O)C=CC=1 KRFRLPRRZHLQDL-UHFFFAOYSA-N 0.000 claims 2
- CGGZGXALPDLUCC-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=O)O)C=CC=1F CGGZGXALPDLUCC-UHFFFAOYSA-N 0.000 claims 2
- QLPYOMGYYAPNTB-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-5-(trifluoromethyl)benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=O)O)C=C(C=1)C(F)(F)F QLPYOMGYYAPNTB-UHFFFAOYSA-N 0.000 claims 2
- VNVBDQOPTQKPNV-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-5-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=O)O)C=C(C=1)F VNVBDQOPTQKPNV-UHFFFAOYSA-N 0.000 claims 2
- KQFKBSJNVWRFDY-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-5-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=O)O)C=C(C=1)OC KQFKBSJNVWRFDY-UHFFFAOYSA-N 0.000 claims 2
- WCGLTFMYGMEKEM-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-5-methylbenzoic acid Chemical compound CC1=CC(=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1)C(O)=O WCGLTFMYGMEKEM-UHFFFAOYSA-N 0.000 claims 2
- WLSQQQFVCWASFK-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-5-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC(=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1)C(O)=O WLSQQQFVCWASFK-UHFFFAOYSA-N 0.000 claims 2
- JCDWBUNJPCRIKN-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=O)O)C=CC=1 JCDWBUNJPCRIKN-UHFFFAOYSA-N 0.000 claims 2
- NGPYCTNCDHXSHB-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]quinoline-8-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=NC2=C(C=CC=C2C=1)C(=O)O NGPYCTNCDHXSHB-UHFFFAOYSA-N 0.000 claims 2
- ITHXHZGUFHHOMA-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxymethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(COCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1 ITHXHZGUFHHOMA-UHFFFAOYSA-N 0.000 claims 2
- XJPBANNKNSFKOE-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]bicyclo[2.2.2]octane-1-carbonyl]amino]-5-(trifluoromethyl)benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(=O)NC=1C=C(C(=O)O)C=C(C=1)C(F)(F)F XJPBANNKNSFKOE-UHFFFAOYSA-N 0.000 claims 2
- NYAOHXSBAWQFOZ-UHFFFAOYSA-N 3-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]methoxy]-5-(trifluoromethyl)benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COCC12CCC(CC1)(CC2)COC=1C=C(C(=O)O)C=C(C=1)C(F)(F)F NYAOHXSBAWQFOZ-UHFFFAOYSA-N 0.000 claims 2
- XIZRNZVRNRWSFT-UHFFFAOYSA-N 3-[[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]bicyclo[2.2.2]octane-1-carbonyl]amino]methyl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(=O)NCC=1C=C(C(=O)O)C=CC=1 XIZRNZVRNRWSFT-UHFFFAOYSA-N 0.000 claims 2
- RVNRQGDQWVLPNS-UHFFFAOYSA-N 3-cyclobutyloxy-5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=C(OC2CCC2)C=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=N1 RVNRQGDQWVLPNS-UHFFFAOYSA-N 0.000 claims 2
- FGMDFCILNHZMHB-UHFFFAOYSA-N 4-(cyclobutylmethoxy)-6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]quinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2C(OCC2CCC2)=C1 FGMDFCILNHZMHB-UHFFFAOYSA-N 0.000 claims 2
- MWGLJKWWPIPPFU-BQYQJAHWSA-N 4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-1-methylindole-2-carboxylic acid Chemical compound CN1C(=CC2=C(\C=C\C34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=CC=C12)C(O)=O MWGLJKWWPIPPFU-BQYQJAHWSA-N 0.000 claims 2
- RSTHOGFJRGIBNW-BQYQJAHWSA-N 4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]benzoic acid Chemical compound OC(=O)C1=CC=C(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1 RSTHOGFJRGIBNW-BQYQJAHWSA-N 0.000 claims 2
- MCGUGGTZDFCMEC-HWKANZROSA-N 4-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1 MCGUGGTZDFCMEC-HWKANZROSA-N 0.000 claims 2
- RSRQPPUCNAFDTM-UHFFFAOYSA-N 4-[2-(chloromethyl)-3-hydroxypropoxy]-6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]quinoline-2-carboxylic acid Chemical compound OCC(CCl)COC1=CC(=NC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C12)C(O)=O RSRQPPUCNAFDTM-UHFFFAOYSA-N 0.000 claims 2
- KZPIZJOOJNXZEA-UHFFFAOYSA-N 4-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1H-indole-6-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=CN2)C(=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 KZPIZJOOJNXZEA-UHFFFAOYSA-N 0.000 claims 2
- GIWJDTCXTLGCDY-UHFFFAOYSA-N 4-[3-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NC(=NO1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 GIWJDTCXTLGCDY-UHFFFAOYSA-N 0.000 claims 2
- ZRVBOYFDBQSGOI-UHFFFAOYSA-N 4-[3-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NOC(=N1)C1=CC(=NC=C1)C(=O)O ZRVBOYFDBQSGOI-UHFFFAOYSA-N 0.000 claims 2
- PZVQMSBIHKPIAA-UHFFFAOYSA-N 4-[3-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NC(=NO1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1OC(F)(F)F)C1CC1 PZVQMSBIHKPIAA-UHFFFAOYSA-N 0.000 claims 2
- WMURSFMOBYNJQS-UHFFFAOYSA-N 4-[3-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC(=C1)C1=NC(=NO1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1OC(F)(F)F)C1CC1 WMURSFMOBYNJQS-UHFFFAOYSA-N 0.000 claims 2
- CMPUCDNLNFAGBQ-UHFFFAOYSA-N 4-[3-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)C(F)(F)F)COC12CCC(CC1)(CC2)C1=NOC(=N1)C1=CC=C(C(=O)O)C=C1 CMPUCDNLNFAGBQ-UHFFFAOYSA-N 0.000 claims 2
- HTWAKCUDAAATHL-UHFFFAOYSA-N 4-[3-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC(=C1)C1=NC(=NO1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1C(F)(F)F)C1CC1 HTWAKCUDAAATHL-UHFFFAOYSA-N 0.000 claims 2
- YIYQGXGZPYLUAG-UHFFFAOYSA-N 4-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COCC12CCC(CC1)(CC2)C1=CC=C(C(=O)O)C=C1 YIYQGXGZPYLUAG-UHFFFAOYSA-N 0.000 claims 2
- OARCYHJFTQEWHN-UHFFFAOYSA-N 4-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C12CCC(COCC3=C(ON=C3C3=C(Cl)C=CC=C3Cl)C3CC3)(CC1)CO2 OARCYHJFTQEWHN-UHFFFAOYSA-N 0.000 claims 2
- WEIJCVCCSSGFFL-UHFFFAOYSA-N 4-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-8-(trifluoromethyl)quinoline-6-carboxylic acid Chemical compound OC(=O)C1=CC2=C(N=CC=C2C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(=C1)C(F)(F)F WEIJCVCCSSGFFL-UHFFFAOYSA-N 0.000 claims 2
- FCHMBRXQZPIBEH-UHFFFAOYSA-N 4-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]benzoic acid Chemical compound OC(=O)c1ccc(cc1)C12CCC(COCc3c(onc3-c3ccccc3OC(F)(F)F)C3CC3)(CC1)CO2 FCHMBRXQZPIBEH-UHFFFAOYSA-N 0.000 claims 2
- AEJICVPURLCZSH-UHFFFAOYSA-N 4-[4-[[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]amino]methyl]-2-oxabicyclo[2.2.2]octan-1-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)NCC12COC(CC1)(CC2)C1=CC=C(C(=O)O)C=C1 AEJICVPURLCZSH-UHFFFAOYSA-N 0.000 claims 2
- CMRFXFLXJJYIOY-UHFFFAOYSA-N 4-[5-[4-[[3-(4-chloro-2-methylpyrazol-3-yl)-5-cyclopropyl-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-6-methoxypyridine-2-carboxylic acid Chemical compound ClC=1C=NN(C=1C1=NOC(=C1COC12CCC(CC1)(CC2)C1=NC(=NO1)C1=CC(=NC(=C1)OC)C(=O)O)C1CC1)C CMRFXFLXJJYIOY-UHFFFAOYSA-N 0.000 claims 2
- FOFXFNYIVXFEAT-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 FOFXFNYIVXFEAT-UHFFFAOYSA-N 0.000 claims 2
- AJQUFYGEEBGKRH-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C1=CC(=NC=C1)C(=O)O AJQUFYGEEBGKRH-UHFFFAOYSA-N 0.000 claims 2
- GWDLVBWIPFNXBN-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-2-oxabicyclo[2.2.2]octan-1-yl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CO2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 GWDLVBWIPFNXBN-UHFFFAOYSA-N 0.000 claims 2
- MWORYOAEBQFXDR-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(COCC3=C(ON=C3C3=C(Cl)C=CC=C3Cl)C3CC3)(CC1)CC2 MWORYOAEBQFXDR-UHFFFAOYSA-N 0.000 claims 2
- MLGMMJBEJLQBQE-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(COCC3=C(ON=C3C3=C(Cl)C=CC=C3Cl)C3CC3)(CC1)CO2 MLGMMJBEJLQBQE-UHFFFAOYSA-N 0.000 claims 2
- BLWSFOHIXSETRP-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)triazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(N=NN1C1=C(Cl)C=CC=C1Cl)C1CC1 BLWSFOHIXSETRP-UHFFFAOYSA-N 0.000 claims 2
- GCLGNJFXKDPAQS-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-6-propan-2-yloxypyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C1=CC(=NC(=C1)OC(C)C)C(=O)O GCLGNJFXKDPAQS-UHFFFAOYSA-N 0.000 claims 2
- ROQSCVHIZWPAQX-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-2-oxabicyclo[2.2.2]octan-1-yl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CO2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 ROQSCVHIZWPAQX-UHFFFAOYSA-N 0.000 claims 2
- OPWPEQHRUFBAMC-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC(=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1OC(F)(F)F)C1CC1 OPWPEQHRUFBAMC-UHFFFAOYSA-N 0.000 claims 2
- WMFDVCAPMHVISM-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-2-oxabicyclo[2.2.2]octan-1-yl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CO2)OCC1=C(ON=C1C1=C(OC(F)(F)F)C=CC=C1)C1CC1 WMFDVCAPMHVISM-UHFFFAOYSA-N 0.000 claims 2
- IDWDGORIBPSEQT-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(COCC3=C(ON=C3C3=CC=CC=C3OC(F)(F)F)C3CC3)(CC1)CC2 IDWDGORIBPSEQT-UHFFFAOYSA-N 0.000 claims 2
- JEXYEJHTRXRUMP-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1C(F)(F)F)C1CC1 JEXYEJHTRXRUMP-UHFFFAOYSA-N 0.000 claims 2
- OEHBBTWYSFNXKA-UHFFFAOYSA-N 4-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC(=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1C(F)(F)F)C1CC1 OEHBBTWYSFNXKA-UHFFFAOYSA-N 0.000 claims 2
- SIFRMFSRTSVHJF-UHFFFAOYSA-N 4-[5-[4-[[5-propan-2-yl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound CC(C)C1=C(COC23CCC(CC2)(CC3)C2=NC(=NO2)C2=CC=C(C=C2)C(O)=O)C(=NO1)C1=CC=CC=C1OC(F)(F)F SIFRMFSRTSVHJF-UHFFFAOYSA-N 0.000 claims 2
- GWVFONNDXDMUIX-UHFFFAOYSA-N 4-[5-[4-[[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]amino]methyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CNC3=C(ON=C3C3=C(Cl)C=CC=C3Cl)C3CC3)(CC1)CC2 GWVFONNDXDMUIX-UHFFFAOYSA-N 0.000 claims 2
- QUKDBOMNJLPTSZ-UHFFFAOYSA-N 4-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-hydroxymethyl]-3-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(C1=C(C=C(C(=O)O)C=C1)F)O QUKDBOMNJLPTSZ-UHFFFAOYSA-N 0.000 claims 2
- BJPAPGXPJJWCSW-UHFFFAOYSA-N 4-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-hydroxymethyl]quinoline-7-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(C1=CC=NC2=CC(=CC=C12)C(=O)O)O BJPAPGXPJJWCSW-UHFFFAOYSA-N 0.000 claims 2
- PWFHKZKKGCMAME-UHFFFAOYSA-N 4-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=CC=C(C(=O)O)C=C1 PWFHKZKKGCMAME-UHFFFAOYSA-N 0.000 claims 2
- QQGPZJBHNOXQIW-UHFFFAOYSA-N 4-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-methoxybenzoic acid Chemical compound COC1=C(C=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1)C(O)=O QQGPZJBHNOXQIW-UHFFFAOYSA-N 0.000 claims 2
- ARFRUQUUKHDZFT-UHFFFAOYSA-N 4-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1)C(F)(F)F ARFRUQUUKHDZFT-UHFFFAOYSA-N 0.000 claims 2
- AFCCCYPAVZDHFQ-UHFFFAOYSA-N 4-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=C(C=C(C(=O)O)C=C1)F AFCCCYPAVZDHFQ-UHFFFAOYSA-N 0.000 claims 2
- FQIZYXUKQARSKS-UHFFFAOYSA-N 4-[[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]isoquinoline-1-carboxylic acid Chemical compound OC(=O)C1=C2C=CC=CC2=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=CC=CC=C2C(F)(F)F)C2CC2)C=N1 FQIZYXUKQARSKS-UHFFFAOYSA-N 0.000 claims 2
- MDNDHAAVHUUPEM-UHFFFAOYSA-N 4-[[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]bicyclo[2.2.2]octane-1-carbonyl]amino]methyl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(=O)NCC1=CC=C(C(=O)O)C=C1 MDNDHAAVHUUPEM-UHFFFAOYSA-N 0.000 claims 2
- FPODYWBPWRTPBY-UHFFFAOYSA-N 4-cyclobutyloxy-6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]quinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=C(C=C(C=C2)C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(OC2CCC2)=C1 FPODYWBPWRTPBY-UHFFFAOYSA-N 0.000 claims 2
- KSGCZEYUPFFYGI-UHFFFAOYSA-N 4-cyclobutyloxy-6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-8-fluoroquinoline-2-carboxylic acid Chemical compound C1(CCC1)OC1=CC(=NC2=C(C=C(C=C12)OCC12CCC(CC1)(CC2)OCC=1C(=NOC=1C1CC1)C1=C(C=NC=C1Cl)Cl)F)C(=O)O KSGCZEYUPFFYGI-UHFFFAOYSA-N 0.000 claims 2
- AIOLYNAVGXTJAS-UHFFFAOYSA-N 4-cyclobutyloxy-6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]quinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2C(OC2CCC2)=C1 AIOLYNAVGXTJAS-UHFFFAOYSA-N 0.000 claims 2
- KZNMJSLLSRSUOV-MDZDMXLPSA-N 4-cyclopentyloxy-6-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]quinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=C(C=C(\C=C\C34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2)C(OC2CCCC2)=C1 KZNMJSLLSRSUOV-MDZDMXLPSA-N 0.000 claims 2
- CDCFRCQSTWSJEV-UHFFFAOYSA-N 4-cyclopropyl-6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-8-fluoroquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=CC(=NC2=C(C=C(C=C12)OCC12CCC(CC1)(CC2)OCC=1C(=NOC=1C1CC1)C1=C(C=NC=C1Cl)Cl)F)C(=O)O CDCFRCQSTWSJEV-UHFFFAOYSA-N 0.000 claims 2
- ZZVZUHIALJOOAG-ONEGZZNKSA-N 5-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(\C=C\C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1 ZZVZUHIALJOOAG-ONEGZZNKSA-N 0.000 claims 2
- HMOFYJHMANKUQJ-UHFFFAOYSA-N 5-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1H-indazole-7-carboxylic acid Chemical compound OC(=O)C1=C2NN=CC2=CC(=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 HMOFYJHMANKUQJ-UHFFFAOYSA-N 0.000 claims 2
- KUSMNRGZYMYFLR-UHFFFAOYSA-N 5-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-2-methoxybenzoic acid Chemical compound COC1=C(C=C(C=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O KUSMNRGZYMYFLR-UHFFFAOYSA-N 0.000 claims 2
- WLIMYGZPVUOUPU-UHFFFAOYSA-N 5-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-3-methylpyridine-2-carboxylic acid Chemical compound CC1=CC(=CN=C1C(O)=O)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 WLIMYGZPVUOUPU-UHFFFAOYSA-N 0.000 claims 2
- TXZNQMHNBYFICC-UHFFFAOYSA-N 5-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-4-methylpyridine-2-carboxylic acid Chemical compound CC1=CC(=NC=C1C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O TXZNQMHNBYFICC-UHFFFAOYSA-N 0.000 claims 2
- AVBJOMCHKWSEJJ-UHFFFAOYSA-N 5-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-6-(4-methylpiperazin-1-yl)pyridine-3-carboxylic acid Chemical compound CN1CCN(CC1)C1=NC=C(C=C1C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O AVBJOMCHKWSEJJ-UHFFFAOYSA-N 0.000 claims 2
- QFWMXSJSFILRBU-UHFFFAOYSA-N 5-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-6-methoxypyridine-3-carboxylic acid Chemical compound COC1=NC=C(C=C1C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O QFWMXSJSFILRBU-UHFFFAOYSA-N 0.000 claims 2
- BVRVONYNOJFEIX-UHFFFAOYSA-N 5-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=NC=C(N=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 BVRVONYNOJFEIX-UHFFFAOYSA-N 0.000 claims 2
- BHBFVDMFPOJDNC-UHFFFAOYSA-N 5-[3-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]-2-methylpyrazole-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NOC(=N1)C1=NN(C(=C1)C(=O)O)C BHBFVDMFPOJDNC-UHFFFAOYSA-N 0.000 claims 2
- UTSCVCPBMKAODD-UHFFFAOYSA-N 5-[4-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,3-oxazol-2-yl]-2-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1N=C(OC=1)C=1C=CC(=C(C(=O)O)C=1)OC UTSCVCPBMKAODD-UHFFFAOYSA-N 0.000 claims 2
- UJUBDXMUXAZMJA-UHFFFAOYSA-N 5-[4-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,3-thiazol-2-yl]-2-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1N=C(SC=1)C=1C=CC(=C(C(=O)O)C=1)OC UJUBDXMUXAZMJA-UHFFFAOYSA-N 0.000 claims 2
- JDAOYDDDSNTGHH-UHFFFAOYSA-N 5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C(=O)N JDAOYDDDSNTGHH-UHFFFAOYSA-N 0.000 claims 2
- RSRGOYBWOBFVLU-UHFFFAOYSA-N 5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]-2-fluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC(=C1)C12CCC(COCC3=C(ON=C3C3=C(Cl)C=CC=C3Cl)C3CC3)(CC1)CO2 RSRGOYBWOBFVLU-UHFFFAOYSA-N 0.000 claims 2
- YMCZNWCHVOBTPB-UHFFFAOYSA-N 5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxymethyl]-2-oxabicyclo[2.2.2]octan-1-yl]-2-fluorobenzoic acid Chemical compound OC(=O)c1cc(ccc1F)C12CCC(COCc3c(onc3-c3ccccc3OC(F)(F)F)C3CC3)(CC1)CO2 YMCZNWCHVOBTPB-UHFFFAOYSA-N 0.000 claims 2
- BLTHHBGIZDYSGE-UHFFFAOYSA-N 5-[5-[4-[[3-(4-chloro-2-methylpyrazol-3-yl)-5-cyclopropyl-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-methoxybenzoic acid Chemical compound ClC=1C=NN(C=1C1=NOC(=C1COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=CC(=C(C(=O)O)C=1)OC)C1CC1)C BLTHHBGIZDYSGE-UHFFFAOYSA-N 0.000 claims 2
- JRVUMRYYCKYECS-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=CC(=C(C(=O)O)C=1)F JRVUMRYYCKYECS-UHFFFAOYSA-N 0.000 claims 2
- DIEZEEGCLMMFQD-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-methoxybenzoic acid Chemical compound COC1=C(C=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1)C(O)=O DIEZEEGCLMMFQD-UHFFFAOYSA-N 0.000 claims 2
- ZXZIQBCDKQBELO-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 ZXZIQBCDKQBELO-UHFFFAOYSA-N 0.000 claims 2
- QRLMUZGBVACLIR-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 QRLMUZGBVACLIR-UHFFFAOYSA-N 0.000 claims 2
- NJHGZVVWFOCOIT-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-2-oxabicyclo[2.2.2]octan-1-yl]-1,2,4-oxadiazol-3-yl]-2-fluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC(=C1)C1=NOC(=N1)C12CCC(CC1)(CO2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 NJHGZVVWFOCOIT-UHFFFAOYSA-N 0.000 claims 2
- PXMMCIJJPZGEDM-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=CC(=C(C(=O)O)C=1)F PXMMCIJJPZGEDM-UHFFFAOYSA-N 0.000 claims 2
- USHJTZXZAGPBFH-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-methoxy-N-methylsulfonylbenzamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=CC(=C(C(=O)NS(=O)(=O)C)C=1)OC USHJTZXZAGPBFH-UHFFFAOYSA-N 0.000 claims 2
- LCSVEGBYCMYDKD-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=CC(=C(C(=O)O)C=1)OC LCSVEGBYCMYDKD-UHFFFAOYSA-N 0.000 claims 2
- OLQGSCLODSDUHN-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-methoxypyridine-3-carboxylic acid Chemical compound COC1=NC=C(C=C1C(O)=O)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 OLQGSCLODSDUHN-UHFFFAOYSA-N 0.000 claims 2
- FKIOEQDWVYUFPH-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-propan-2-yloxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=CC(=C(C(=O)O)C=1)OC(C)C FKIOEQDWVYUFPH-UHFFFAOYSA-N 0.000 claims 2
- ZVYCIBWSDREYGY-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-3-fluoro-2-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=C(C(=O)O)C=1)OC)F ZVYCIBWSDREYGY-UHFFFAOYSA-N 0.000 claims 2
- IAFBSDYCVALMRX-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1H-imidazol-2-yl]-2-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1N=C(NC=1)C=1C=CC(=C(C(=O)O)C=1)OC IAFBSDYCVALMRX-UHFFFAOYSA-N 0.000 claims 2
- DWZYVFYSQDDYMA-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-2-oxabicyclo[2.2.2]octan-1-yl]-1,2,4-oxadiazol-3-yl]-2-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12COC(CC1)(CC2)C1=NC(=NO1)C=1C=CC(=C(C(=O)O)C=1)OC DWZYVFYSQDDYMA-UHFFFAOYSA-N 0.000 claims 2
- VVYCSMMIVOYHDI-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=CC(=NC=1)C(=O)O VVYCSMMIVOYHDI-UHFFFAOYSA-N 0.000 claims 2
- WTNPWTUTRJHPAM-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1OC(F)(F)F)C1CC1 WTNPWTUTRJHPAM-UHFFFAOYSA-N 0.000 claims 2
- YCGGCEABKZAAJT-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]-2-methoxybenzoic acid Chemical compound COC1=C(C=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1C(F)(F)F)C1CC1)C(O)=O YCGGCEABKZAAJT-UHFFFAOYSA-N 0.000 claims 2
- ULQXKUPCZCEAAN-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1C(F)(F)F)C1CC1 ULQXKUPCZCEAAN-UHFFFAOYSA-N 0.000 claims 2
- MRAAWNFQBGUXFU-UHFFFAOYSA-N 5-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)C(F)(F)F)COC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=NC=C(C(=O)O)C=1 MRAAWNFQBGUXFU-UHFFFAOYSA-N 0.000 claims 2
- LMRCIZRWNVSOGK-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-fluorobenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=CC(=C(C(=O)O)C=1)F LMRCIZRWNVSOGK-UHFFFAOYSA-N 0.000 claims 2
- ABFMZSZMWTXJCO-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=NC=C(C(=O)O)C=1 ABFMZSZMWTXJCO-UHFFFAOYSA-N 0.000 claims 2
- CMMRGCPKNDCTPD-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methylamino]-2-methylpyrazole-3-carboxylic acid Chemical compound Cn1nc(NCC23CCC(CC2)(CC3)OCc2c(onc2-c2c(Cl)cccc2Cl)C2CC2)cc1C(O)=O CMMRGCPKNDCTPD-UHFFFAOYSA-N 0.000 claims 2
- XBNVIGFWWMLPML-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methylamino]pyridine-3-carboxylic acid Chemical compound OC(=O)c1cncc(NCC23CCC(CC2)(CC3)OCc2c(onc2-c2c(Cl)cccc2Cl)C2CC2)c1 XBNVIGFWWMLPML-UHFFFAOYSA-N 0.000 claims 2
- XZNNOPZSBQJCQR-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-1-ethyl-4-fluoropyrazole-3-carboxylic acid Chemical compound CCN1N=C(C(O)=O)C(F)=C1OCC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 XZNNOPZSBQJCQR-UHFFFAOYSA-N 0.000 claims 2
- NWGNUPKHTNBRHW-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-1-ethylpyrazole-3-carboxylic acid Chemical compound CCN1N=C(C=C1OCC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O NWGNUPKHTNBRHW-UHFFFAOYSA-N 0.000 claims 2
- ONYOCMBSPOTMDK-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-1-methylpyrazole-3-carboxylic acid Chemical compound CN1N=C(C=C1OCC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O ONYOCMBSPOTMDK-UHFFFAOYSA-N 0.000 claims 2
- QXFCVSGVIHMYJM-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2,4-dimethylpyrazole-3-carboxylic acid Chemical compound CN1N=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(C)=C1C(O)=O QXFCVSGVIHMYJM-UHFFFAOYSA-N 0.000 claims 2
- OTCIKYBWJGVFDZ-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-(cyclopropylmethyl)-4-fluoropyrazole-3-carboxylic acid Chemical compound OC(=O)C1=C(F)C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=NN1CC1CC1 OTCIKYBWJGVFDZ-UHFFFAOYSA-N 0.000 claims 2
- GFAHBVBVQXMMOO-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-(cyclopropylmethyl)-4-methylpyrazole-3-carboxylic acid Chemical compound CC1=C(N(CC2CC2)N=C1OCC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O GFAHBVBVQXMMOO-UHFFFAOYSA-N 0.000 claims 2
- SOQZOLPXBTWPRC-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-(cyclopropylmethyl)pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=NN1CC1CC1 SOQZOLPXBTWPRC-UHFFFAOYSA-N 0.000 claims 2
- PUKKTSYWAPQYSF-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-ethyl-4-methylpyrazole-3-carboxylic acid Chemical compound CCN1N=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(C)=C1C(O)=O PUKKTSYWAPQYSF-UHFFFAOYSA-N 0.000 claims 2
- TWQDLGSODLDKLH-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-ethylpyrazole-3-carboxylic acid Chemical compound CCN1N=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1C(O)=O TWQDLGSODLDKLH-UHFFFAOYSA-N 0.000 claims 2
- BDMBFJYSCVHMGG-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-fluorobenzoic acid Chemical compound OC(=O)C1=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=CC=C1F BDMBFJYSCVHMGG-UHFFFAOYSA-N 0.000 claims 2
- ZIMSWRDTSMLLEI-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-methylpyrazole-3-carboxylic acid Chemical compound CN1N=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1C(O)=O ZIMSWRDTSMLLEI-UHFFFAOYSA-N 0.000 claims 2
- DXJIDCXCBNRCAX-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-(1,1-difluoroethyl)pyridine-2-carboxylic acid Chemical compound CC(F)(F)C1=C(N=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1)C(O)=O DXJIDCXCBNRCAX-UHFFFAOYSA-N 0.000 claims 2
- IYERYRYLSVIEBW-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-(2,2,2-trifluoroethoxy)pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=NC=1)C(=O)O)OCC(F)(F)F IYERYRYLSVIEBW-UHFFFAOYSA-N 0.000 claims 2
- DLMNWXCTCNZVLS-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-(2-methoxyethoxy)pyridine-2-carboxylic acid Chemical compound COCCOC1=C(N=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1)C(O)=O DLMNWXCTCNZVLS-UHFFFAOYSA-N 0.000 claims 2
- PYAADOMRMGVDPC-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-(cyclopropylmethoxy)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=C(OCC2CC2)C=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=N1 PYAADOMRMGVDPC-UHFFFAOYSA-N 0.000 claims 2
- KNJSJIQZZCMTMQ-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-(methoxymethyl)pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=NC=1)C(=O)O)COC KNJSJIQZZCMTMQ-UHFFFAOYSA-N 0.000 claims 2
- DFJRNGSOAMODNW-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-(trifluoromethyl)pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=NC=1)C(=O)O)C(F)(F)F DFJRNGSOAMODNW-UHFFFAOYSA-N 0.000 claims 2
- BRCIBDPAOCHJJV-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-cyclopropyloxypyridine-2-carboxylic acid Chemical compound OC(=O)C1=C(OC2CC2)C=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=N1 BRCIBDPAOCHJJV-UHFFFAOYSA-N 0.000 claims 2
- JJLQSTCTEGETJB-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-ethoxypyridine-2-carboxamide Chemical compound CCOC1=C(N=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1)C(N)=O JJLQSTCTEGETJB-UHFFFAOYSA-N 0.000 claims 2
- CJSIRNJGHHRFIU-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-ethoxypyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=NC=1)C(=O)O)OCC CJSIRNJGHHRFIU-UHFFFAOYSA-N 0.000 claims 2
- ZHPQPBOLIUCJQY-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-methoxypyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=NC=1)C(=O)O)OC ZHPQPBOLIUCJQY-UHFFFAOYSA-N 0.000 claims 2
- YVJKQRJAVRTJTD-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-methylpyridine-2-carboxamide Chemical compound CC1=C(N=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C1)C(N)=O YVJKQRJAVRTJTD-UHFFFAOYSA-N 0.000 claims 2
- RKLAKDFPMMYWJC-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-methylpyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=NC=1)C(=O)O)C RKLAKDFPMMYWJC-UHFFFAOYSA-N 0.000 claims 2
- GAOJINMGTKCGQC-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-propan-2-yloxypyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C(C(=NC=1)C(=O)O)OC(C)C GAOJINMGTKCGQC-UHFFFAOYSA-N 0.000 claims 2
- NDUJNEHQDYWIJJ-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-methyl-2-(oxetan-3-ylmethyl)pyrazole-3-carboxylic acid Chemical compound CC1=C(N(CC2COC2)N=C1OCC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O NDUJNEHQDYWIJJ-UHFFFAOYSA-N 0.000 claims 2
- YREQNBLIVBLKFB-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-methyl-2-propan-2-ylpyrazole-3-carboxylic acid Chemical compound CC(C)N1N=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(C)=C1C(O)=O YREQNBLIVBLKFB-UHFFFAOYSA-N 0.000 claims 2
- NIXOPQWMHLWRJT-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=N1 NIXOPQWMHLWRJT-UHFFFAOYSA-N 0.000 claims 2
- NGAMUSYLUKWVFP-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-2-fluorobenzoic acid Chemical compound OC(=O)C1=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=CC=CC=C2C(F)(F)F)C2CC2)=CC=C1F NGAMUSYLUKWVFP-UHFFFAOYSA-N 0.000 claims 2
- RCUKLBOMCGLIRX-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-ethoxypyridine-2-carboxamide Chemical compound CCOC1=C(N=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=CC=CC=C2C(F)(F)F)C2CC2)=C1)C(N)=O RCUKLBOMCGLIRX-UHFFFAOYSA-N 0.000 claims 2
- SFATYYDKFQXOFL-UHFFFAOYSA-N 5-[[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-ethoxypyridine-2-carboxylic acid Chemical compound CCOC1=C(N=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=CC=CC=C2C(F)(F)F)C2CC2)=C1)C(O)=O SFATYYDKFQXOFL-UHFFFAOYSA-N 0.000 claims 2
- WPEGGCDSUBAHHX-UHFFFAOYSA-N 5-cyclopropyl-3-(2,6-dichlorophenyl)-4-[[1-[3-(2H-tetrazol-5-yl)phenyl]-2-oxabicyclo[2.2.2]octan-4-yl]methoxymethyl]-1,2-oxazole Chemical compound N1N=NN=C1C=1C=C(C=CC=1)C12OCC(CC1)(CC2)COCC=1C(=NOC=1C1CC1)C1=C(C=CC=C1Cl)Cl WPEGGCDSUBAHHX-UHFFFAOYSA-N 0.000 claims 2
- UAISDRDPOMMDTE-BQYQJAHWSA-N 5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-4-[[4-[(E)-2-[4-(2H-tetrazol-5-ylmethyl)phenyl]ethenyl]-1-bicyclo[2.2.2]octanyl]oxymethyl]-1,2-oxazole Chemical compound ClC1=CN=CC(Cl)=C1C1=NOC(C2CC2)=C1COC12CCC(CC1)(CC2)\C=C\C1=CC=C(CC2=NNN=N2)C=C1 UAISDRDPOMMDTE-BQYQJAHWSA-N 0.000 claims 2
- OTPPXGVHWDQPCH-UHFFFAOYSA-N 6-(azetidin-1-yl)-5-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=C(N2CCC2)C(=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 OTPPXGVHWDQPCH-UHFFFAOYSA-N 0.000 claims 2
- STEFUOFHVMYJLH-VOTSOKGWSA-N 6-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-1-methylindole-2-carboxylic acid Chemical compound CN1C(=CC2=C1C=C(\C=C\C13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2)C(O)=O STEFUOFHVMYJLH-VOTSOKGWSA-N 0.000 claims 2
- IHHXTFZSKFIHQX-BQYQJAHWSA-N 6-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-4-ethoxyquinoline-2-carboxylic acid Chemical compound CCOC1=CC(=NC2=C1C=C(\C=C\C13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2)C(O)=O IHHXTFZSKFIHQX-BQYQJAHWSA-N 0.000 claims 2
- OCBYPFJVLBHLAY-VOTSOKGWSA-N 6-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-4-methoxyquinazoline-2-carboxylic acid Chemical compound COC1=NC(=NC2=C1C=C(\C=C\C13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2)C(O)=O OCBYPFJVLBHLAY-VOTSOKGWSA-N 0.000 claims 2
- XMHVVIZKDIEWNV-BQYQJAHWSA-N 6-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-4-propan-2-yloxyquinoline-2-carboxylic acid Chemical compound CC(C)OC1=CC(=NC2=C1C=C(\C=C\C13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2)C(O)=O XMHVVIZKDIEWNV-BQYQJAHWSA-N 0.000 claims 2
- CQRYVQKGTVZFLZ-AATRIKPKSA-N 6-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]imidazo[1,2-a]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=C2C=CC(\C=C\C34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)=CN12 CQRYVQKGTVZFLZ-AATRIKPKSA-N 0.000 claims 2
- JYRFKQFUBIKIRL-BQYQJAHWSA-N 6-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]quinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=C(C=C1)C=C(\C=C\C13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2 JYRFKQFUBIKIRL-BQYQJAHWSA-N 0.000 claims 2
- OHJIDDZOPJSSLT-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethyl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)CCC=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F OHJIDDZOPJSSLT-UHFFFAOYSA-N 0.000 claims 2
- KUVGDRNPGBBSQX-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethyl]-4-propan-2-yloxyquinoline-2-carboxylic acid Chemical compound CC(C)OC1=CC(=NC2=C1C=C(CCC13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2)C(O)=O KUVGDRNPGBBSQX-UHFFFAOYSA-N 0.000 claims 2
- KGHFOIQKADFXOR-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethyl]quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)CCC=1C=C2C=CC(=NC2=CC=1)C(=O)O KGHFOIQKADFXOR-UHFFFAOYSA-N 0.000 claims 2
- FISSJEHGGPTWRB-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-(3-methoxypropoxy)isoquinoline-3-carboxylic acid Chemical compound COCCCOC1=NC(=CC2=CC(=CC=C12)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O FISSJEHGGPTWRB-UHFFFAOYSA-N 0.000 claims 2
- QUCCUFPTCRJMDF-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-(4-methylpiperazin-1-yl)isoquinoline-3-carboxylic acid Chemical compound CN1CCN(CC1)C1=NC(=CC2=CC(=CC=C12)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O QUCCUFPTCRJMDF-UHFFFAOYSA-N 0.000 claims 2
- VGLMCUAPQNXBMX-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-methylpyrrolo[2,3-b]pyridine-3-carboxylic acid Chemical compound CN1C=C(C(O)=O)C2=CC=C(N=C12)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 VGLMCUAPQNXBMX-UHFFFAOYSA-N 0.000 claims 2
- FACWXGBOTJWNEG-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-morpholin-4-ylisoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=CC(=CC=C2C(=N1)N1CCOCC1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 FACWXGBOTJWNEG-UHFFFAOYSA-N 0.000 claims 2
- UWVTWSJJCWMSBX-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1H-indazole-4-carboxylic acid Chemical compound OC(=O)c1cc(cc2[nH]ncc12)C#CC12CCC(CC1)(CC2)OCc1c(onc1-c1c(Cl)cncc1Cl)C1CC1 UWVTWSJJCWMSBX-UHFFFAOYSA-N 0.000 claims 2
- FVZHZZXEIXDCAU-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1H-indole-4-carboxylic acid Chemical compound OC(=O)c1cc(cc2[nH]ccc12)C#CC12CCC(CC1)(CC2)OCc1c(onc1-c1c(Cl)cncc1Cl)C1CC1 FVZHZZXEIXDCAU-UHFFFAOYSA-N 0.000 claims 2
- XJTSSGUDXBLJOX-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-2-methylpyridine-3-carboxylic acid Chemical compound CC1=NC(=CC=C1C(O)=O)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 XJTSSGUDXBLJOX-UHFFFAOYSA-N 0.000 claims 2
- IJOYJGSRLYNGHX-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-4-(difluoromethoxy)quinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=C(C=C(C=C2)C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(OC(F)F)=C1 IJOYJGSRLYNGHX-UHFFFAOYSA-N 0.000 claims 2
- VEPGBJRNMANROF-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-4-(trifluoromethyl)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(=CC(=N1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(F)(F)F VEPGBJRNMANROF-UHFFFAOYSA-N 0.000 claims 2
- FCWPHZAWBUUALF-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-4-(trifluoromethyl)pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=C1C(F)(F)F)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 FCWPHZAWBUUALF-UHFFFAOYSA-N 0.000 claims 2
- UNSXJCDEVKZFJC-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound C1=2C(=CC(=NC1=CC=C(C#CC13CCC(CC1)(OCC=1C(C4=C(Cl)C=NC=C4Cl)=NOC=1C1CC1)CC3)C=2)C(=O)O)C(F)(F)F UNSXJCDEVKZFJC-UHFFFAOYSA-N 0.000 claims 2
- BPUYJUCMMUUXKG-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-4-methoxypyridine-2-carboxylic acid Chemical compound COC1=CC(=NC(=C1)C(O)=O)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 BPUYJUCMMUUXKG-UHFFFAOYSA-N 0.000 claims 2
- BZPWHHFXRALUHJ-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-4-methoxyquinoline-2-carboxylic acid Chemical compound COC1=CC(=NC2=C1C=C(C=C2)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O BZPWHHFXRALUHJ-UHFFFAOYSA-N 0.000 claims 2
- BFOLGAJGUQFTOJ-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-4-propan-2-yloxyquinoline-2-carboxylic acid Chemical compound CC(C)OC1=CC(=NC2=C1C=C(C=C2)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O BFOLGAJGUQFTOJ-UHFFFAOYSA-N 0.000 claims 2
- BENHBDMPSKAHBL-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-5-fluoropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=C(C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(F)=C1 BENHBDMPSKAHBL-UHFFFAOYSA-N 0.000 claims 2
- OUAGUFBGXYYMER-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]imidazo[1,2-a]pyridine-8-carboxylic acid Chemical compound OC(=O)C1=CC(=CN2C=CN=C12)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 OUAGUFBGXYYMER-UHFFFAOYSA-N 0.000 claims 2
- DVDFNRLZPAAJID-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]pyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(N=N1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 DVDFNRLZPAAJID-UHFFFAOYSA-N 0.000 claims 2
- KNOVNWAKJBUTEO-UHFFFAOYSA-N 6-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]quinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C=C2C=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 KNOVNWAKJBUTEO-UHFFFAOYSA-N 0.000 claims 2
- VBGZNCZTIODECK-UHFFFAOYSA-N 6-[3-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(=N1)C1=NC(=NO1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 VBGZNCZTIODECK-UHFFFAOYSA-N 0.000 claims 2
- UZGHOHSXZJBXCY-UHFFFAOYSA-N 6-[3-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(=N1)C1=NC(=NO1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1OC(F)(F)F)C1CC1 UZGHOHSXZJBXCY-UHFFFAOYSA-N 0.000 claims 2
- QDCSPAMDZWYZGW-UHFFFAOYSA-N 6-[3-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-5-yl]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)C(F)(F)F)COC12CCC(CC1)(CC2)C1=NOC(=N1)C1=CC=CC(=N1)C(=O)O QDCSPAMDZWYZGW-UHFFFAOYSA-N 0.000 claims 2
- KDPCKLDIXCMJIH-UHFFFAOYSA-N 6-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,5-naphthyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C=1N=C2C=CC(=NC2=CC=1)C(=O)O KDPCKLDIXCMJIH-UHFFFAOYSA-N 0.000 claims 2
- MJHFNWJSCIZWMS-UHFFFAOYSA-N 6-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1-methylpyrrolo[2,3-b]pyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=CC=C2C(=N1)N(C=C2C(=O)O)C MJHFNWJSCIZWMS-UHFFFAOYSA-N 0.000 claims 2
- XIQUUUJGRSAHID-UHFFFAOYSA-N 6-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]pyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC=C(C(=O)O)C=C1 XIQUUUJGRSAHID-UHFFFAOYSA-N 0.000 claims 2
- LWZWXVPIBBUZCS-UHFFFAOYSA-N 6-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,5-naphthyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC2=C(C=C1)N=C(C=C2)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 LWZWXVPIBBUZCS-UHFFFAOYSA-N 0.000 claims 2
- JUOLNUVICVSFOF-UHFFFAOYSA-N 6-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1-ethylpyrazolo[3,4-b]pyridine-3-carboxylic acid Chemical compound CCN1N=C(C(O)=O)C2=CC=C(N=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 JUOLNUVICVSFOF-UHFFFAOYSA-N 0.000 claims 2
- URZCSQZZYMCUTH-UHFFFAOYSA-N 6-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1-methylpyrazolo[3,4-b]pyridine-3-carboxylic acid Chemical compound CN1N=C(C(O)=O)C2=CC=C(N=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 URZCSQZZYMCUTH-UHFFFAOYSA-N 0.000 claims 2
- LXOJWNYSHPQEMU-UHFFFAOYSA-N 6-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C1=CC=CC(=N1)C(=O)O LXOJWNYSHPQEMU-UHFFFAOYSA-N 0.000 claims 2
- XFNUKWLRGXKOHH-UHFFFAOYSA-N 6-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)C1=CC=CC(=N1)C(=O)O XFNUKWLRGXKOHH-UHFFFAOYSA-N 0.000 claims 2
- CMJQZWWRGNZDMC-UHFFFAOYSA-N 6-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(=N1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1OC(F)(F)F)C1CC1 CMJQZWWRGNZDMC-UHFFFAOYSA-N 0.000 claims 2
- AOYIMGUJDVAAOL-UHFFFAOYSA-N 6-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1OC(F)(F)F)C1CC1 AOYIMGUJDVAAOL-UHFFFAOYSA-N 0.000 claims 2
- DZPUBFBGNVJPJQ-UHFFFAOYSA-N 6-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(=N1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1C(F)(F)F)C1CC1 DZPUBFBGNVJPJQ-UHFFFAOYSA-N 0.000 claims 2
- JKPLCBNWFFIWTP-UHFFFAOYSA-N 6-[[4-[[3-(3-chloro-5-methoxypyridin-4-yl)-5-cyclopropyl-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-3-methylpyridine-2-carboxylic acid Chemical compound ClC=1C=NC=C(C=1C1=NOC(=C1COC12CCC(CC1)(CC2)COC1=CC=C(C(=N1)C(=O)O)C)C1CC1)OC JKPLCBNWFFIWTP-UHFFFAOYSA-N 0.000 claims 2
- LKBUNXXRBNUZIG-UHFFFAOYSA-N 6-[[4-[[3-(3-chloro-5-methoxypyridin-4-yl)-5-cyclopropyl-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-methylpyridine-3-carboxylic acid Chemical compound ClC=1C=NC=C(C=1C1=NOC(=C1COC12CCC(CC1)(CC2)COC1=NC=C(C(=O)O)C(=C1)C)C1CC1)OC LKBUNXXRBNUZIG-UHFFFAOYSA-N 0.000 claims 2
- TZAKSOREWJSVGG-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-hydroxymethyl]naphthalene-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C(C=1C=C2C=CC(=CC2=CC=1)C(=O)O)O TZAKSOREWJSVGG-UHFFFAOYSA-N 0.000 claims 2
- QNGXXBUVPJMLSB-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-1-methylindole-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=CC=C2C(=CN(C2=C1)C)C(=O)O QNGXXBUVPJMLSB-UHFFFAOYSA-N 0.000 claims 2
- LLFVOWYCDQTFOQ-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F LLFVOWYCDQTFOQ-UHFFFAOYSA-N 0.000 claims 2
- JVJQBNMFLWJKGS-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyrazine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=CN=CC(=N1)C(=O)O JVJQBNMFLWJKGS-UHFFFAOYSA-N 0.000 claims 2
- OHCUYDYCGPDIPC-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyridine-2-carboxamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=CC=CC(=N1)C(=O)N OHCUYDYCGPDIPC-UHFFFAOYSA-N 0.000 claims 2
- XCNAMCFSOUZOFB-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=CC=CC(=N1)C(=O)O XCNAMCFSOUZOFB-UHFFFAOYSA-N 0.000 claims 2
- KPBJBOHVGKQDTP-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=NC=C(C(=O)O)C=C1 KPBJBOHVGKQDTP-UHFFFAOYSA-N 0.000 claims 2
- VMPROHZLTYVFOR-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-1,5-naphthyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1N=C2C=CC(=NC2=CC=1)C(=O)O VMPROHZLTYVFOR-UHFFFAOYSA-N 0.000 claims 2
- YWKIRXJMCGIMOM-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-1-methylindole-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=CC=C2C(=CN(C2=C1)C)C(=O)O YWKIRXJMCGIMOM-UHFFFAOYSA-N 0.000 claims 2
- JEJMNPWJFXSVTN-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(2-methylpropoxy)quinoline-2-carboxylic acid Chemical compound CC(C)COC1=CC(=NC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C12)C(O)=O JEJMNPWJFXSVTN-UHFFFAOYSA-N 0.000 claims 2
- GODFICYVBREPEH-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(3-methoxyazetidin-1-yl)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1)C(=O)O)N1CC(C1)OC GODFICYVBREPEH-UHFFFAOYSA-N 0.000 claims 2
- LEQOJNMSKIRROL-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(cyclopropylmethoxy)-7-fluoroquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1F)C(=O)O)OCC1CC1 LEQOJNMSKIRROL-UHFFFAOYSA-N 0.000 claims 2
- AFPROGJJEKEZEQ-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(cyclopropylmethoxy)quinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2C(OCC2CC2)=C1 AFPROGJJEKEZEQ-UHFFFAOYSA-N 0.000 claims 2
- HQGPWGYDCIJFKC-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(difluoromethoxy)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC(F)F HQGPWGYDCIJFKC-UHFFFAOYSA-N 0.000 claims 2
- KRUFBCCMOLEMGI-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(oxetan-3-ylmethoxy)quinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2C(OCC2COC2)=C1 KRUFBCCMOLEMGI-UHFFFAOYSA-N 0.000 claims 2
- NJSGVLUIYNRMLB-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(oxetan-3-yloxy)quinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2C(OC2COC2)=C1 NJSGVLUIYNRMLB-UHFFFAOYSA-N 0.000 claims 2
- SSSWRKXUHQHDEW-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(trifluoromethyl)pyridine-3-carboxylic acid Chemical compound OC(=O)C1=C(C=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)N=C1)C(F)(F)F SSSWRKXUHQHDEW-UHFFFAOYSA-N 0.000 claims 2
- PPEDFXXWSUZXSG-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F PPEDFXXWSUZXSG-UHFFFAOYSA-N 0.000 claims 2
- YBPASDREEFQDEN-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-cyclopropyloxyquinoline-2-carboxylic acid Chemical compound C1(CC1)OC1=CC(=NC2=CC=C(C=C12)OCC12CCC(CC1)(CC2)OCC=1C(=NOC=1C1CC1)C1=C(C=NC=C1Cl)Cl)C(=O)O YBPASDREEFQDEN-UHFFFAOYSA-N 0.000 claims 2
- IBPDZMRFYXTMIG-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-ethoxy-7-fluoroquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1F)C(=O)O)OCC IBPDZMRFYXTMIG-UHFFFAOYSA-N 0.000 claims 2
- MHIBKXCBYXMDST-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-ethoxy-8-fluoroquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=C(C=1)F)C(=O)O)OCC MHIBKXCBYXMDST-UHFFFAOYSA-N 0.000 claims 2
- SROOWOWZERCJKU-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-ethoxyquinoline-2-carboxylic acid Chemical compound CCOC1=CC(=NC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C12)C(O)=O SROOWOWZERCJKU-UHFFFAOYSA-N 0.000 claims 2
- GTKZANGPNBCQCM-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-ethylquinoline-2-carboxylic acid Chemical compound CCC1=CC(=NC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C12)C(O)=O GTKZANGPNBCQCM-UHFFFAOYSA-N 0.000 claims 2
- XHXAGNNTFOAPQP-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-methoxypyridine-2-carboxylic acid Chemical compound COC1=CC(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=NC(=C1)C(O)=O XHXAGNNTFOAPQP-UHFFFAOYSA-N 0.000 claims 2
- SINTWJMSZIZWDB-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-methoxypyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=NC=C(C(=O)O)C(=C1)OC SINTWJMSZIZWDB-UHFFFAOYSA-N 0.000 claims 2
- IDHYHTJHJDQQJC-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-methoxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC IDHYHTJHJDQQJC-UHFFFAOYSA-N 0.000 claims 2
- SYYLCGIHANJJDM-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-methylsulfonylquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1)C(=O)O)S(=O)(=O)C SYYLCGIHANJJDM-UHFFFAOYSA-N 0.000 claims 2
- UQPVNESMQGSVPN-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-oxo-1H-quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1)C(=O)O)O UQPVNESMQGSVPN-UHFFFAOYSA-N 0.000 claims 2
- KGVLTKTXRFHOQF-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-propan-2-yloxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC(C)C KGVLTKTXRFHOQF-UHFFFAOYSA-N 0.000 claims 2
- QJRZPTBGIRHTPX-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-propylquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1)C(=O)O)CCC QJRZPTBGIRHTPX-UHFFFAOYSA-N 0.000 claims 2
- DTEBNIMQQGDJEM-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-5-fluoropyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=NC=C(C(=O)O)C=C1F DTEBNIMQQGDJEM-UHFFFAOYSA-N 0.000 claims 2
- JYAHYSPNAAVSLZ-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-8-fluoro-4-(oxetan-3-yloxy)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=C(C=1)F)C(=O)O)OC1COC1 JYAHYSPNAAVSLZ-UHFFFAOYSA-N 0.000 claims 2
- WUEHDPQNJKMDJS-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-8-fluoro-4-methylquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=C(C=1)F)C(=O)O)C WUEHDPQNJKMDJS-UHFFFAOYSA-N 0.000 claims 2
- MBYZYARPQUOHDN-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-8-fluoro-4-propan-2-yloxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=C(C=1)F)C(=O)O)OC(C)C MBYZYARPQUOHDN-UHFFFAOYSA-N 0.000 claims 2
- OWWQJHFEDXHNQR-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-8-fluoro-4-propylquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=C(C=1)F)C(=O)O)CCC OWWQJHFEDXHNQR-UHFFFAOYSA-N 0.000 claims 2
- JQAWTOGHWFIYHD-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-N-methylsulfonyl-4-(trifluoromethyl)quinoline-2-carboxamide Chemical compound CS(=O)(=O)NC(=O)c1cc(c2cc(OCC34CCC(CC3)(CC4)OCc3c(onc3-c3c(Cl)cncc3Cl)C3CC3)ccc2n1)C(F)(F)F JQAWTOGHWFIYHD-UHFFFAOYSA-N 0.000 claims 2
- FZEXMBSEHOHXAE-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=CC=2N(N=1)C(=CN=2)C#N FZEXMBSEHOHXAE-UHFFFAOYSA-N 0.000 claims 2
- TZUHLNVGYYTVSF-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]imidazo[1,2-b]pyridazine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=CC=2N(N=1)C(=CN=2)C(=O)O TZUHLNVGYYTVSF-UHFFFAOYSA-N 0.000 claims 2
- MBQCELYAKCNSLA-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=CC=CC(=N1)C(=O)O MBQCELYAKCNSLA-UHFFFAOYSA-N 0.000 claims 2
- PGLDMULBIRRRNY-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]pyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC1=NC=C(C(=O)O)C=C1 PGLDMULBIRRRNY-UHFFFAOYSA-N 0.000 claims 2
- HKLCQDDOPWQVSB-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)COC=1C=C2C=CC(=NC2=CC=1)C(=O)O HKLCQDDOPWQVSB-UHFFFAOYSA-N 0.000 claims 2
- FFHAOOKVOPSHCO-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxymethyl]-4-(trifluoromethyl)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC(COCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=CC(=C1)C(F)(F)F FFHAOOKVOPSHCO-UHFFFAOYSA-N 0.000 claims 2
- OYPJXVNKEXEFGZ-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-2-oxabicyclo[2.2.2]octan-1-yl]methoxy]-4-(difluoromethoxy)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12COC(CC1)(CC2)COC=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC(F)F OYPJXVNKEXEFGZ-UHFFFAOYSA-N 0.000 claims 2
- GMWOGVFLSCQHJC-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=CC=CC=C3C(F)(F)F)C3CC3)C=C2C(=C1)C(F)(F)F GMWOGVFLSCQHJC-UHFFFAOYSA-N 0.000 claims 2
- VIJZTGRVAYCBSJ-UHFFFAOYSA-N 6-[[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-4-methoxyquinoline-2-carboxylic acid Chemical compound COC1=CC(=NC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=CC=CC=C3C(F)(F)F)C3CC3)C=C12)C(O)=O VIJZTGRVAYCBSJ-UHFFFAOYSA-N 0.000 claims 2
- AMXXRXOALPXPBH-UHFFFAOYSA-N 6-cyclobutyloxy-4-[5-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]pyridine-2-carboxylic acid Chemical compound C1(CCC1)OC1=CC(=CC(=N1)C(=O)O)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC=1C(=NOC=1C1CC1)C1=C(C=NC=C1Cl)Cl AMXXRXOALPXPBH-UHFFFAOYSA-N 0.000 claims 2
- MCRKSMWUNWGFAU-AATRIKPKSA-N 7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-1-(3-fluoroazetidin-1-yl)isoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(\C=C\C34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2)C(=N1)N1CC(F)C1 MCRKSMWUNWGFAU-AATRIKPKSA-N 0.000 claims 2
- FABVVWZJGKTMKZ-AATRIKPKSA-N 7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-1-(3-hydroxyazetidin-1-yl)isoquinoline-3-carboxylic acid Chemical compound OC1CN(C1)C1=NC(=CC2=C1C=C(\C=C\C13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2)C(O)=O FABVVWZJGKTMKZ-AATRIKPKSA-N 0.000 claims 2
- TYJGIQVKKHAZHS-VOTSOKGWSA-N 7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-1-(3-methoxyazetidin-1-yl)isoquinoline-3-carboxylic acid Chemical compound COC1CN(C1)C1=NC(=CC2=C1C=C(\C=C\C13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2)C(O)=O TYJGIQVKKHAZHS-VOTSOKGWSA-N 0.000 claims 2
- ZAVPYEOKYCLCSH-BQYQJAHWSA-N 7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-1-(3-methoxypropoxy)isoquinoline-3-carboxylic acid Chemical compound COCCCOC1=NC(=CC2=C1C=C(\C=C\C13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2)C(O)=O ZAVPYEOKYCLCSH-BQYQJAHWSA-N 0.000 claims 2
- VFEBUNAVRGTMPU-AATRIKPKSA-N 7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-1-[3-(hydroxymethyl)azetidin-1-yl]isoquinoline-3-carboxylic acid Chemical compound OCC1CN(C1)C1=NC(=CC2=C1C=C(\C=C\C13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2)C(O)=O VFEBUNAVRGTMPU-AATRIKPKSA-N 0.000 claims 2
- MZBGAKNKNVCBPG-BQYQJAHWSA-N 7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-1-cyclopropyloxyisoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(\C=C\C34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2)C(OC2CC2)=N1 MZBGAKNKNVCBPG-BQYQJAHWSA-N 0.000 claims 2
- PHXBORMTXKNQBY-BQYQJAHWSA-N 7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-1-ethoxyisoquinoline-3-carboxylic acid Chemical compound CCOC1=NC(=CC2=C1C=C(\C=C\C13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2)C(O)=O PHXBORMTXKNQBY-BQYQJAHWSA-N 0.000 claims 2
- LNKFLVYZFNTXSH-AATRIKPKSA-N 7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-1-morpholin-4-ylisoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(\C=C\C34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2)C(=N1)N1CCOCC1 LNKFLVYZFNTXSH-AATRIKPKSA-N 0.000 claims 2
- ZYODQZJZOOPZDO-HWKANZROSA-N 7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]imidazo[1,2-a]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=C2C=C(\C=C\C34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=CN12 ZYODQZJZOOPZDO-HWKANZROSA-N 0.000 claims 2
- GZPUGVNZOVCVCT-UHFFFAOYSA-N 7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-(2-pyrrolidin-1-ylethoxy)isoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(C=C2)C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(OCCN2CCCC2)=N1 GZPUGVNZOVCVCT-UHFFFAOYSA-N 0.000 claims 2
- HCUVUOYNAMYMGZ-UHFFFAOYSA-N 7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-(3-fluoroazetidin-1-yl)isoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(C=C2)C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(=N1)N1CC(F)C1 HCUVUOYNAMYMGZ-UHFFFAOYSA-N 0.000 claims 2
- DAQIIRPVWHWLAI-UHFFFAOYSA-N 7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-(3-hydroxyazetidin-1-yl)isoquinoline-3-carboxylic acid Chemical compound OC1CN(C1)C1=NC(=CC2=C1C=C(C=C2)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O DAQIIRPVWHWLAI-UHFFFAOYSA-N 0.000 claims 2
- RMRNPIYWZQJVSA-UHFFFAOYSA-N 7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-(3-hydroxypyrrolidin-1-yl)isoquinoline-3-carboxylic acid Chemical compound OC1CCN(C1)C1=NC(=CC2=C1C=C(C=C2)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O RMRNPIYWZQJVSA-UHFFFAOYSA-N 0.000 claims 2
- FPYFQCXZXGLGLT-UHFFFAOYSA-N 7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-(4-hydroxypiperidin-1-yl)isoquinoline-3-carboxylic acid Chemical compound OC1CCN(CC1)C1=NC(=CC2=C1C=C(C=C2)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O FPYFQCXZXGLGLT-UHFFFAOYSA-N 0.000 claims 2
- OIPCKFACUTZLCI-UHFFFAOYSA-N 7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-[3-(dimethylamino)azetidin-1-yl]isoquinoline-3-carboxylic acid Chemical compound CN(C)C1CN(C1)C1=NC(=CC2=C1C=C(C=C2)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C(O)=O OIPCKFACUTZLCI-UHFFFAOYSA-N 0.000 claims 2
- UUIOGVRAZSXXNM-UHFFFAOYSA-N 7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-methoxyisoquinoline-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)COC12CCC(CC1)(CC2)C#CC1=CC=C2C=C(N=C(C2=C1)OC)C(=O)O UUIOGVRAZSXXNM-UHFFFAOYSA-N 0.000 claims 2
- YTFFITIOBXGTDI-UHFFFAOYSA-N 7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-morpholin-4-ylisoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(C=C2)C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(=N1)N1CCOCC1 YTFFITIOBXGTDI-UHFFFAOYSA-N 0.000 claims 2
- WEDCERDTHIVAIY-UHFFFAOYSA-N 7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]-1-piperazin-1-ylisoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C(C=C2)C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(=N1)N1CCNCC1 WEDCERDTHIVAIY-UHFFFAOYSA-N 0.000 claims 2
- UJBZFBGSKXDOMB-UHFFFAOYSA-N 7-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]imidazo[1,2-a]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CN2C=CC(=CC2=N1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 UJBZFBGSKXDOMB-UHFFFAOYSA-N 0.000 claims 2
- TVMKOQXOKATKAL-UHFFFAOYSA-N 7-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-1-ethoxyisoquinoline-3-carboxylic acid Chemical compound CCOC1=NC(=CC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C12)C(O)=O TVMKOQXOKATKAL-UHFFFAOYSA-N 0.000 claims 2
- SUAVWWBKNLTFBI-UHFFFAOYSA-N 7-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]-1-ethylisoquinoline-3-carboxylic acid Chemical compound CCC1=NC(=CC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C12)C(O)=O SUAVWWBKNLTFBI-UHFFFAOYSA-N 0.000 claims 2
- FDHGGOLHSWEJMP-UHFFFAOYSA-N 7-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]isoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=C(OCC34CCC(CC3)(CC4)OCC3=C(ON=C3C3=C(Cl)C=NC=C3Cl)C3CC3)C=C2C=N1 FDHGGOLHSWEJMP-UHFFFAOYSA-N 0.000 claims 2
- ROWGGXHYZOKNRE-UHFFFAOYSA-N 7-chloro-1-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]isoquinoline-3-carboxylic acid Chemical compound OC(=O)C1=NC(C#CC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)=C2C=C(Cl)C=CC2=C1 ROWGGXHYZOKNRE-UHFFFAOYSA-N 0.000 claims 2
- UIWMZEUVMWOTNT-UHFFFAOYSA-N 8-[2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethynyl]quinoline-5-carboxylic acid Chemical compound OC(=O)C1=C2C=CC=NC2=C(C=C1)C#CC12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 UIWMZEUVMWOTNT-UHFFFAOYSA-N 0.000 claims 2
- YGXWIWKYJUSMQH-UHFFFAOYSA-N 8-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]quinoline-5-carboxylic acid Chemical compound OC(=O)C1=C2C=CC=NC2=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C=C1 YGXWIWKYJUSMQH-UHFFFAOYSA-N 0.000 claims 2
- SAOIVFMCMRLOPD-UHFFFAOYSA-N 8-[[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]quinoline-5-carboxylic acid Chemical compound OC(=O)C1=C2C=CC=NC2=C(OCC23CCC(CC2)(CC3)OCC2=C(ON=C2C2=CC=CC=C2C(F)(F)F)C2CC2)C=C1 SAOIVFMCMRLOPD-UHFFFAOYSA-N 0.000 claims 2
- QTKLZFBAUPDCBN-UHFFFAOYSA-N 8-chloro-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-6-methoxyquinoline-5-carboxylic acid Chemical compound COC1=C(C(O)=O)C2=C(N=C(C=C2)C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(Cl)=C1 QTKLZFBAUPDCBN-UHFFFAOYSA-N 0.000 claims 2
- SPIMLZZZZRKZIC-UHFFFAOYSA-N 8-chloro-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-6-propan-2-yloxyquinoline-5-carboxylic acid Chemical compound CC(C)OC1=C(C(O)=O)C2=C(N=C(C=C2)C23CCC(CC2)(CC3)OCC2=C(ON=C2C2=C(Cl)C=NC=C2Cl)C2CC2)C(Cl)=C1 SPIMLZZZZRKZIC-UHFFFAOYSA-N 0.000 claims 2
- YPWDJYRSYDWICV-UHFFFAOYSA-N 8-chloro-6-cyclobutyloxy-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]quinoline-5-carboxylic acid Chemical compound OC(=O)C1=C(OC2CCC2)C=C(Cl)C2=C1C=CC(=N2)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 YPWDJYRSYDWICV-UHFFFAOYSA-N 0.000 claims 2
- CDXOPRYHQWXKBA-UHFFFAOYSA-N 8-cyano-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]quinoline-5-carboxylic acid Chemical compound C(#N)C1=CC=C(C=2C=CC(=NC1=2)C12CCC(CC1)(CC2)OCC=1C(=NOC=1C1CC1)C1=C(C=NC=C1Cl)Cl)C(=O)O CDXOPRYHQWXKBA-UHFFFAOYSA-N 0.000 claims 2
- MZEPUGKXGDBXTQ-UHFFFAOYSA-N 8-cyclobutyloxy-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]quinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC=C(OC2CCC2)C2=NC(=CC=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 MZEPUGKXGDBXTQ-UHFFFAOYSA-N 0.000 claims 2
- KSQYXXHEKGGTCB-UHFFFAOYSA-N 8-cyclobutyloxy-2-[[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]methoxy]quinoline-5-carboxylic acid Chemical compound C1(CCC1)OC1=CC=C(C=2C=CC(=NC1=2)OCC12CCC(CC1)(CC2)OCC=1C(=NOC=1C1CC1)C1=C(C=NC=C1Cl)Cl)C(=O)O KSQYXXHEKGGTCB-UHFFFAOYSA-N 0.000 claims 2
- WAMNDRORUJZBBV-UHFFFAOYSA-N 8-cyclopentyloxy-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]quinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC=C(OC2CCCC2)C2=NC(=CC=C12)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1 WAMNDRORUJZBBV-UHFFFAOYSA-N 0.000 claims 2
- JPOQQUGIOXZHPJ-UHFFFAOYSA-N 8-cyclopropyl-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]quinoline-5-carboxylic acid Chemical compound C1(CC1)C1=CC=C(C=2C=CC(=NC1=2)C12CCC(CC1)(CC2)OCC=1C(=NOC=1C1CC1)C1=C(C=NC=C1Cl)Cl)C(=O)O JPOQQUGIOXZHPJ-UHFFFAOYSA-N 0.000 claims 2
- RWKMIFJFMVXMQJ-UHFFFAOYSA-N 8-cyclopropyl-2-[4-[[5-cyclopropyl-3-(dicyclopropylmethyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]quinoline-5-carboxylic acid Chemical compound OC(=O)C1=CC=C(C2CC2)C2=C1C=CC(=N2)C12CCC(CC1)(CC2)OCC1=C(ON=C1C(C1CC1)C1CC1)C1CC1 RWKMIFJFMVXMQJ-UHFFFAOYSA-N 0.000 claims 2
- PEDNHFLGOMRXRQ-UHFFFAOYSA-N N-(benzenesulfonyl)-4-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NOC(C2CC2)=C1COC12CCC(CC1)(CC2)C1=NC(=NO1)C1=CC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=CC=C1 PEDNHFLGOMRXRQ-UHFFFAOYSA-N 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- GZBSUNIYGVGJSU-UHFFFAOYSA-N [5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]methanol Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)COC12CCC(CC1)(CC2)C1=NC(=NO1)CO GZBSUNIYGVGJSU-UHFFFAOYSA-N 0.000 claims 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 2
- 230000002500 effect on skin Effects 0.000 claims 2
- VDFSIQSDJNIOOD-UHFFFAOYSA-N methyl 3-[5-[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoate Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C=CC12CCC(CC1)(CC2)C1=NC(=NO1)C=1C=C(C(=O)OC)C=CC=1 VDFSIQSDJNIOOD-UHFFFAOYSA-N 0.000 claims 2
- WLJZSKDVUWJILT-UHFFFAOYSA-N methyl 3-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoate Chemical compound COC(=O)C1=CC=CC(=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1C(F)(F)F)C1CC1 WLJZSKDVUWJILT-UHFFFAOYSA-N 0.000 claims 2
- OYHWOVSMSSOPTI-UHFFFAOYSA-N methyl 3-[[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]bicyclo[2.2.1]heptane-1-carbonyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC(=O)C23CCC(CC2)(C3)C=CC2=C(ON=C2C2=C(Cl)C=CC=C2Cl)C2CC2)=C1 OYHWOVSMSSOPTI-UHFFFAOYSA-N 0.000 claims 2
- OABNPDIAOXPPFP-UHFFFAOYSA-N methyl 3-[[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]bicyclo[2.2.2]octane-1-carbonyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC(=O)C23CCC(CC2)(CC3)C=CC2=C(ON=C2C2=C(Cl)C=CC=C2Cl)C2CC2)=C1 OABNPDIAOXPPFP-UHFFFAOYSA-N 0.000 claims 2
- VAALVAPJLHCRIN-UHFFFAOYSA-N methyl 3-chloro-4-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]bicyclo[2.2.2]octane-1-carbonyl]amino]benzoate Chemical compound ClC=1C=C(C(=O)OC)C=CC=1NC(=O)C12CCC(CC1)(CC2)COCC=1C(=NOC=1C1CC1)C1=C(C=CC=C1Cl)Cl VAALVAPJLHCRIN-UHFFFAOYSA-N 0.000 claims 2
- IZDNXPRTQBDGNZ-UHFFFAOYSA-N methyl 3-chloro-4-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxymethyl]bicyclo[2.2.2]octane-1-carbothioyl]amino]benzoate Chemical compound ClC=1C=C(C(=O)OC)C=CC=1NC(=S)C12CCC(CC1)(CC2)COCC=1C(=NOC=1C1CC1)C1=C(C=CC=C1Cl)Cl IZDNXPRTQBDGNZ-UHFFFAOYSA-N 0.000 claims 2
- HKUGDXUNGFHYQO-UHFFFAOYSA-N methyl 4-[4-[[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]amino]methyl]-2-oxabicyclo[2.2.2]octan-1-yl]benzoate Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)NCC12COC(CC1)(CC2)C1=CC=C(C(=O)OC)C=C1 HKUGDXUNGFHYQO-UHFFFAOYSA-N 0.000 claims 2
- FTBVBXJOIYFYTH-UHFFFAOYSA-N methyl 4-[5-[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]-1-bicyclo[2.2.1]heptanyl]-1,2,4-oxadiazol-3-yl]benzoate Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C=CC12CCC(CC1)(C2)C1=NC(=NO1)C1=CC=C(C(=O)OC)C=C1 FTBVBXJOIYFYTH-UHFFFAOYSA-N 0.000 claims 2
- XFHPDROGGNEIBG-UHFFFAOYSA-N methyl 4-[5-[4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)C=CC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 XFHPDROGGNEIBG-UHFFFAOYSA-N 0.000 claims 2
- VASOJHSFFLJWJP-UHFFFAOYSA-N methyl 4-[5-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=C(Cl)C=CC=C1Cl)C1CC1 VASOJHSFFLJWJP-UHFFFAOYSA-N 0.000 claims 2
- VYHXQXXUUBJWMT-UHFFFAOYSA-N methyl 4-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxymethyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(COCC3=C(ON=C3C3=CC=CC=C3OC(F)(F)F)C3CC3)(CC1)CC2 VYHXQXXUUBJWMT-UHFFFAOYSA-N 0.000 claims 2
- MIRSFJZHVONBQT-UHFFFAOYSA-N methyl 4-[5-[4-[[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1C(F)(F)F)C1CC1 MIRSFJZHVONBQT-UHFFFAOYSA-N 0.000 claims 2
- UPYLQWAYRZZESB-UHFFFAOYSA-N methyl 4-[5-[4-[[5-propan-2-yl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazol-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(C=C1)C1=NOC(=N1)C12CCC(CC1)(CC2)OCC1=C(ON=C1C1=CC=CC=C1OC(F)(F)F)C(C)C UPYLQWAYRZZESB-UHFFFAOYSA-N 0.000 claims 2
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- HFUUIPMSPWIDDU-VOTSOKGWSA-N 7-[(E)-2-[4-[[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]methoxy]-1-bicyclo[2.2.2]octanyl]ethenyl]-1-(4-methylpiperazin-1-yl)isoquinoline-3-carboxylic acid Chemical compound CN1CCN(CC1)C1=NC(=CC2=C1C=C(\C=C\C13CCC(CC1)(CC3)OCC1=C(ON=C1C1=C(Cl)C=NC=C1Cl)C1CC1)C=C2)C(O)=O HFUUIPMSPWIDDU-VOTSOKGWSA-N 0.000 claims 1
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- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
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- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
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- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| US201762580075P | 2017-11-01 | 2017-11-01 | |
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| PCT/US2018/058315 WO2019089667A1 (en) | 2017-11-01 | 2018-10-31 | Bridged bicyclic compounds as farnesoid x receptor modulators |
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| KR20200081434A KR20200081434A (ko) | 2020-07-07 |
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| CN110128432B (zh) | 2018-02-02 | 2021-03-02 | 广东东阳光药业有限公司 | 含氮三环化合物及其在药物中的应用 |
| AU2019362753A1 (en) | 2018-10-05 | 2021-05-20 | Vertex Pharmaceuticals Incorporated | Modulators of alpha-1 antitrypsin |
| EA202192275A1 (ru) | 2019-02-15 | 2021-11-03 | Бристол-Маерс Сквибб Компани | Замещенные амидные соединения, полезные в качестве модуляторов фарнезоидного x-рецептора |
| CN113677666A (zh) | 2019-02-15 | 2021-11-19 | 百时美施贵宝公司 | 作为类法尼醇x受体调节剂的经取代的双环化合物 |
| AU2020221371A1 (en) | 2019-02-15 | 2021-10-07 | Bristol-Myers Squibb Company | Substituted amide compounds useful as farnesoid x receptor modulators |
| UY38696A (es) | 2019-05-14 | 2020-11-30 | Vertex Pharma | Moduladores de alfa-1 antitripsina |
| AU2020282759A1 (en) | 2019-05-31 | 2021-12-23 | Ikena Oncology, Inc. | TEAD inhibitors and uses thereof |
| MX2021014443A (es) | 2019-05-31 | 2022-01-06 | Ikena Oncology Inc | Inhibidores del dominio asociado mejorador de la transcripcion (tead) y usos de los mismos. |
| CN110922368B (zh) * | 2019-11-29 | 2022-08-16 | 扬州工业职业技术学院 | 一种氯代苯异噁唑氨基苯甲酸衍生物及其制备方法与应用 |
| CN110804025B (zh) * | 2019-11-29 | 2022-02-08 | 扬州工业职业技术学院 | 一种卤代苯异噁唑衍生物及其制备方法与应用 |
| ES3014367T3 (en) | 2020-01-15 | 2025-04-22 | Inst Nat Sante Rech Med | Use of fxr agonists for treating an infection by hepatitis d virus |
| AU2021246527A1 (en) * | 2020-04-03 | 2022-10-27 | Vertex Pharmaceuticals Incorporated | Modulators of alpha-1 antitrypsin |
| WO2021203014A1 (en) | 2020-04-03 | 2021-10-07 | Vertex Pharmaceuticals Incorporated | Pyrano[4,3-b]l ndole derivatives as alpha-1 -antitrypsin modulators for treating alpha-1 -antitrypsin deficiency (aatd) |
| WO2022120353A1 (en) * | 2020-12-02 | 2022-06-09 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| CA3204800A1 (en) | 2021-01-14 | 2022-07-21 | Raphael Darteil | Synergistic effect of a fxr agonist and ifn for the treatment of hbv infection |
| JP2024517181A (ja) | 2021-04-28 | 2024-04-19 | ウエヌイグレックオ・ファーマ | 組合せ治療としてfxrアゴニストを使用するtlr3アゴニストの効果の強い増強 |
| CN115504972B (zh) * | 2021-06-22 | 2024-11-12 | 广东药科大学 | 异恶唑类衍生物、其制备方法及其作为药物的用途 |
| CA3267500A1 (en) | 2022-09-19 | 2024-03-28 | Basf Se | AZOLE PESTICIDE COMPOUNDS |
| CN117105779A (zh) * | 2023-07-18 | 2023-11-24 | 河南师范大学 | 一种5-溴-2-甲酰基苯甲酸甲酯的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017118294A1 (zh) | 2016-01-06 | 2017-07-13 | 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 |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993013101A1 (fr) | 1991-12-27 | 1993-07-08 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose de pyridonecarboxylate, son utilisation pharmaceutique et compose spiro |
| WO1998017276A1 (en) | 1996-10-25 | 1998-04-30 | Merck & Co., Inc. | Heteroaryl spiroethercycloalkyl tachykinin receptor antagonists |
| BR9910130A (pt) | 1998-04-17 | 2001-01-09 | Kenneth Curry | Derivados de cubana como antagonistas de receptor de glutamato metabotrópico e processo para a sua preparação |
| MXPA02004796A (es) | 1999-11-12 | 2007-01-30 | Biogen Inc | Policicloalquilpurinas como antagonistas del receptor de adenosina. |
| WO2001079261A1 (en) | 2000-04-14 | 2001-10-25 | Corvas International, Inc. | Tetrahydro-azepinone derivatives as thrombin inhibitors |
| ATE360614T1 (de) | 2001-06-21 | 2007-05-15 | Cesare Casagrande | Verbindung für die behandlung von atherosclerotischen und thrombotischen erkrankungen |
| AU2003264018A1 (en) | 2002-08-09 | 2004-02-25 | Astrazeneca Ab | Compounds having an activity at metabotropic glutamate receptors |
| EP1761513A1 (en) | 2004-07-01 | 2007-03-14 | Wyeth | Tetracyclic compounds as estrogen ligands |
| WO2006006490A1 (ja) | 2004-07-08 | 2006-01-19 | Ono Pharmaceutical Co., Ltd. | スピロ化合物 |
| PT2402002T (pt) | 2005-04-08 | 2018-10-08 | Ptc Therapeutics Inc | Composições de 1,2,4-oxadiazole oralmente activo para terapia de supressão de mutações nonsense |
| JP5081161B2 (ja) | 2005-12-19 | 2012-11-21 | スミスクライン ビーチャム コーポレーション | ファルネソイドx受容体アゴニスト |
| KR101470659B1 (ko) | 2006-09-07 | 2014-12-08 | 액테리온 파마슈티칼 리미티드 | 면역조절제로서 피리딘-4-일 유도체 |
| CL2007003035A1 (es) | 2006-10-24 | 2008-05-16 | Smithkline Beechman Corp | Compuestos derivados de isoxazol sustituidos, agonistas de receptores farnesoid x; procedimiento de preparacion; composicion farmaceutica que lo comprende; y uso del compuesto en el tratamiento de la obesidad, diabetes mellitus, fibrosis en organos, |
| EP2108017A2 (en) | 2007-01-30 | 2009-10-14 | Biogen Idec MA, Inc. | Imidazolone compounds as tgf-beta family type i receptors, alk5 and/or alk4 antagonists |
| CA2690406A1 (en) | 2007-07-02 | 2009-01-08 | Glaxosmithkline Llc | Farnesoid x receptor agonists |
| 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 |
| CA2703203C (en) | 2007-10-22 | 2015-12-15 | Schering Corporation | Bicyclic heterocycle derivatives and methods of use thereof |
| US20110230493A1 (en) | 2008-11-21 | 2011-09-22 | Pfizer Inc. | 1-OXA-8-Azaspiro [4,5] Decabe-8-Carboxamide Compounds as FAAH Inhibitors |
| WO2010100142A1 (en) | 2009-03-03 | 2010-09-10 | Merck Serono S.A. | Oxazole pyridine derivatives useful as s1p1 receptor agonists |
| JP5460858B2 (ja) | 2009-05-05 | 2014-04-02 | エフ.ホフマン−ラ ロシュ アーゲー | イソオキサゾール−ピラゾール誘導体 |
| US8440710B2 (en) | 2009-10-15 | 2013-05-14 | Hoffmann-La Roche Inc. | HSL inhibitors useful in the treatment of diabetes |
| TW201300380A (zh) | 2010-10-19 | 2013-01-01 | Comentis Inc | 抑制β-分泌酶活性之噁二唑化合物及其使用方法 |
| CA2818542A1 (en) | 2010-11-19 | 2012-05-24 | Incyte Corporation | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| 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 |
| UA120740C2 (uk) | 2011-04-22 | 2020-02-10 | Сігнал Фармасьютікалз, Елелсі | Заміщені діамінокарбоксамідні і діамінокарбонітрильні похідні піримідинів, їх композиції і способи лікування з їх допомогою |
| EP2520566A1 (en) | 2011-05-06 | 2012-11-07 | Orion Corporation | New Pharmaceutical Compounds |
| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| IN2014DN09346A (enExample) | 2012-06-13 | 2015-07-17 | Hoffmann La Roche | |
| JP6099753B2 (ja) | 2012-10-03 | 2017-03-22 | アドビナス セラピューティクス リミテッド | スピロ環化合物、その組成物及びその医薬応用 |
| US9567301B2 (en) | 2012-11-02 | 2017-02-14 | Dana-Farber Cancer Institute, Inc. | Pyrrol-1-yl benzoic acid derivatives useful as myc inhibitors |
| EP2774919A1 (en) | 2013-03-06 | 2014-09-10 | Pharmeste S.R.L. In Liquidazione | Novel sulfonamide TRPA1 receptor antagonists |
| AU2014244482B2 (en) | 2013-03-14 | 2018-01-25 | Bristol-Myers Squibb Company | Bicyclo [2.2.2] acid GPR120 modulators |
| TW201605859A (zh) | 2013-11-14 | 2016-02-16 | 必治妥美雅史谷比公司 | 作為酪蛋白激酶1δ/ε抑制劑之新穎經取代之吡唑并-哌 |
| WO2015172747A1 (en) | 2014-05-16 | 2015-11-19 | Zhaoyin Wang | Spirocyclic molecules as mth1 inhibitors |
| WO2016073545A1 (en) | 2014-11-06 | 2016-05-12 | Concert Pharmaceuticals, Inc. | Phenyloxadiazole benzoic acids |
| EP3034501A1 (en) * | 2014-12-17 | 2016-06-22 | Gilead Sciences, Inc. | Hydroxy containing FXR (NR1H4) modulating compounds |
| EP3034499A1 (en) | 2014-12-17 | 2016-06-22 | Gilead Sciences, Inc. | Novel 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. |
| SG10201913036RA (en) | 2015-02-20 | 2020-02-27 | Incyte Corp | Bicyclic heterocycles as fgfr inhibitors |
| 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 |
| CN108602811B (zh) | 2016-02-01 | 2021-11-16 | 轩竹生物科技有限公司 | Fxr受体激动剂 |
| 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 |
| SI3419625T1 (sl) | 2016-02-22 | 2021-08-31 | Novartis Ag | Postopki za uporabo agonistov FXR |
| SI3419624T1 (sl) | 2016-02-22 | 2021-05-31 | Novartis Ag | Postopki za uporabo agonistov FXR |
| WO2017189652A1 (en) | 2016-04-26 | 2017-11-02 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as fxr agonists and methods of use thereof |
| US10080742B2 (en) | 2016-04-26 | 2018-09-25 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as FXR agonists and methods of use thereof |
| US10080743B2 (en) | 2016-04-26 | 2018-09-25 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as FXR agonists and methods of use thereof |
| US10149835B2 (en) | 2016-05-18 | 2018-12-11 | Elmore Patent Law Group, P.C. | Isoxazole derivatives as FXR agonists and methods of use thereof |
| WO2017218337A1 (en) | 2016-06-13 | 2017-12-21 | Gilead Sciences, Inc. | Fxr (nr1h4) modulating compounds |
| AR108711A1 (es) | 2016-06-13 | 2018-09-19 | Gilead Sciences Inc | Compuestos moduladores de fxr (nr1h4) |
| WO2018059314A1 (zh) | 2016-09-28 | 2018-04-05 | 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 |
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