HRP20241414T1 - Azabenzimidazolski spojevi i farmaceutski proizvod - Google Patents
Azabenzimidazolski spojevi i farmaceutski proizvod Download PDFInfo
- Publication number
- HRP20241414T1 HRP20241414T1 HRP20241414TT HRP20241414T HRP20241414T1 HR P20241414 T1 HRP20241414 T1 HR P20241414T1 HR P20241414T T HRP20241414T T HR P20241414TT HR P20241414 T HRP20241414 T HR P20241414T HR P20241414 T1 HRP20241414 T1 HR P20241414T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- pyridin
- imidazo
- trifluoromethyl
- amino
- Prior art date
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- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 229940127557 pharmaceutical product Drugs 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 29
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 21
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 21
- 235000019260 propionic acid Nutrition 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 12
- -1 azabenzimidazole compound Chemical class 0.000 claims 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000004385 trihaloalkyl group Chemical group 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- VJZKWBUNZQRBGB-UHFFFAOYSA-N 1-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC(COC)(C)C)C(F)(F)F VJZKWBUNZQRBGB-UHFFFAOYSA-N 0.000 claims 2
- RYSWKPPWKDLVBE-UHFFFAOYSA-N 1-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F RYSWKPPWKDLVBE-UHFFFAOYSA-N 0.000 claims 2
- HSMBTEUILOUESV-UHFFFAOYSA-N 1-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F HSMBTEUILOUESV-UHFFFAOYSA-N 0.000 claims 2
- GOQKHFIDHBXUNH-UHFFFAOYSA-N 1-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(ethoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COCC)C(F)(F)F GOQKHFIDHBXUNH-UHFFFAOYSA-N 0.000 claims 2
- UPHBRDIUZHVFDC-UHFFFAOYSA-N 2-[1-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]oxyacetic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)OCC(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F UPHBRDIUZHVFDC-UHFFFAOYSA-N 0.000 claims 2
- PWFMBXBEMQRVSC-UHFFFAOYSA-N 3-[4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)CCC(=O)O)N(C)CC1(CCCCC1)COC)C(F)(F)F PWFMBXBEMQRVSC-UHFFFAOYSA-N 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 102000017925 CHRM3 Human genes 0.000 claims 2
- 101150060249 CHRM3 gene Proteins 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 229940126027 positive allosteric modulator Drugs 0.000 claims 2
- 230000000069 prophylactic effect Effects 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 208000028394 ureteral disease Diseases 0.000 claims 2
- 208000026533 urinary bladder disease Diseases 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- ZTWNNYCKSFVZIV-UHFFFAOYSA-N 1-[4-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC(COC)(C)C)C(F)(F)F ZTWNNYCKSFVZIV-UHFFFAOYSA-N 0.000 claims 1
- YDKDEOQNUMAHOV-UHFFFAOYSA-N 1-[4-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F YDKDEOQNUMAHOV-UHFFFAOYSA-N 0.000 claims 1
- ZUDMLKJZPPCJII-UHFFFAOYSA-N 1-[4-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCCC1)COC)C(F)(F)F ZUDMLKJZPPCJII-UHFFFAOYSA-N 0.000 claims 1
- OIQXUDNGOOXBFF-UHFFFAOYSA-N 1-[4-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F OIQXUDNGOOXBFF-UHFFFAOYSA-N 0.000 claims 1
- WZQTWAGZCXFSST-UHFFFAOYSA-N 1-[4-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC(COC)(C)C)C(F)(F)F WZQTWAGZCXFSST-UHFFFAOYSA-N 0.000 claims 1
- TXGXKRQUKJTLTP-UHFFFAOYSA-N 1-[4-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCCC1)COC)C(F)(F)F TXGXKRQUKJTLTP-UHFFFAOYSA-N 0.000 claims 1
- FLPJVYKMIWBQJZ-UHFFFAOYSA-N 1-[4-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-fluorophenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=C(C=C(C=C1)N1CCC(CC1)C(=O)O)F)N(C)CC1(CCCC1)COC)C(F)(F)F FLPJVYKMIWBQJZ-UHFFFAOYSA-N 0.000 claims 1
- FSUZLBQVSZGSBU-UHFFFAOYSA-N 1-[4-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F FSUZLBQVSZGSBU-UHFFFAOYSA-N 0.000 claims 1
- RVXZUOFMBRCHJS-UHFFFAOYSA-N 1-[4-[5-[3,5-bis(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)(F)F RVXZUOFMBRCHJS-UHFFFAOYSA-N 0.000 claims 1
- UEVVSYWKTRTCED-UHFFFAOYSA-N 1-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC(COC)(C)C UEVVSYWKTRTCED-UHFFFAOYSA-N 0.000 claims 1
- UAVRGQXGRGLHMT-UHFFFAOYSA-N 1-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]benzoyl]piperidine-4-carboxylic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C(=O)N2CCC(CC2)C(=O)O)C=C1)N(C)CC1(CCC1)COC UAVRGQXGRGLHMT-UHFFFAOYSA-N 0.000 claims 1
- IGAYTVRJGKAJBI-UHFFFAOYSA-N 1-[4-[5-[4-cyclopropyl-3-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F IGAYTVRJGKAJBI-UHFFFAOYSA-N 0.000 claims 1
- WCBQIHUULCLGDH-UHFFFAOYSA-N 1-[4-[5-[4-ethoxy-3-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F WCBQIHUULCLGDH-UHFFFAOYSA-N 0.000 claims 1
- OJEQJNIOSXMLRM-UHFFFAOYSA-N 1-[4-[5-[5,6-bis(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound FC(C=1C=C(C=NC=1C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)(F)F OJEQJNIOSXMLRM-UHFFFAOYSA-N 0.000 claims 1
- NXANZAKSMKRMAU-UHFFFAOYSA-N 1-[4-[5-[5-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C=1C=C(C=NC=1C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCCC1)COC NXANZAKSMKRMAU-UHFFFAOYSA-N 0.000 claims 1
- NVFITWIWYHRGQC-UHFFFAOYSA-N 1-[4-[5-[6-cyano-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(#N)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F NVFITWIWYHRGQC-UHFFFAOYSA-N 0.000 claims 1
- PVTCYJSVVLXTIU-UHFFFAOYSA-N 1-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC(COC)(C)C)C(F)(F)F PVTCYJSVVLXTIU-UHFFFAOYSA-N 0.000 claims 1
- LXKSIXPJMNIEIE-UHFFFAOYSA-N 1-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(ethoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COCC)C(F)(F)F LXKSIXPJMNIEIE-UHFFFAOYSA-N 0.000 claims 1
- OJWJSFDGPNURKA-UHFFFAOYSA-N 1-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F OJWJSFDGPNURKA-UHFFFAOYSA-N 0.000 claims 1
- YXPSLQCCVMWPSC-UHFFFAOYSA-N 1-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F YXPSLQCCVMWPSC-UHFFFAOYSA-N 0.000 claims 1
- XOSORTQIEGQCSX-UHFFFAOYSA-N 1-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-fluorophenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=C(C=C(C=C1)N1CCC(CC1)C(=O)O)F)N(C)CC1(CCC1)COC)C(F)(F)F XOSORTQIEGQCSX-UHFFFAOYSA-N 0.000 claims 1
- MLMUVCNVJNSERI-UHFFFAOYSA-N 1-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-methylphenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=C(C=C(C=C1)N1CCC(CC1)C(=O)O)C)N(C)CC1(CCC1)COC)C(F)(F)F MLMUVCNVJNSERI-UHFFFAOYSA-N 0.000 claims 1
- KYMLQNYIFNEFTO-UHFFFAOYSA-N 1-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F KYMLQNYIFNEFTO-UHFFFAOYSA-N 0.000 claims 1
- RWZVPQQCEUZINH-UHFFFAOYSA-N 1-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-fluorophenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=C(C=C(C=C1)N1CCC(CC1)C(=O)O)F)N(C)CC1(CCCC1)COC)C(F)(F)F RWZVPQQCEUZINH-UHFFFAOYSA-N 0.000 claims 1
- NBNGWKWPYBKCHQ-UHFFFAOYSA-N 1-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F NBNGWKWPYBKCHQ-UHFFFAOYSA-N 0.000 claims 1
- NVJFIZWZCVLTDE-UHFFFAOYSA-N 1-[4-[7-[[1-(ethoxymethyl)cyclopentyl]methyl-methylamino]-5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OCC1(CCCC1)CN(C1=C2C(=NC(=C1)C1=CC(=NC(=C1)C(F)(F)F)OCC)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)C NVJFIZWZCVLTDE-UHFFFAOYSA-N 0.000 claims 1
- QPZIUECQCOIRLN-UHFFFAOYSA-N 1-[4-[7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-5-[3-(trifluoromethyl)phenyl]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]pyrrolidine-3-carboxylic acid Chemical compound COCC1(CCC1)CN(C1=C2C(=NC(=C1)C1=CC(=CC=C1)C(F)(F)F)N=C(N2)C1=CC=C(C=C1)N1CC(CC1)C(=O)O)C QPZIUECQCOIRLN-UHFFFAOYSA-N 0.000 claims 1
- HKMAIRUUCRUBGH-UHFFFAOYSA-N 1-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC(COC)(C)C)C(F)(F)F HKMAIRUUCRUBGH-UHFFFAOYSA-N 0.000 claims 1
- DYWLOKMPEOHKQS-UHFFFAOYSA-N 1-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F DYWLOKMPEOHKQS-UHFFFAOYSA-N 0.000 claims 1
- SFCFBQBQOZMXID-UHFFFAOYSA-N 1-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F SFCFBQBQOZMXID-UHFFFAOYSA-N 0.000 claims 1
- HPPCJPFKWQHFIW-UHFFFAOYSA-N 1-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCCC1)COC)C(F)(F)F HPPCJPFKWQHFIW-UHFFFAOYSA-N 0.000 claims 1
- PGFDWEDEOPHUNV-UHFFFAOYSA-N 1-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)NCC1(CCCC1)COC)C(F)(F)F PGFDWEDEOPHUNV-UHFFFAOYSA-N 0.000 claims 1
- LHOPKJWDEUNDJS-UHFFFAOYSA-N 1-[5-[5-[3-ethoxy-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C(C)OC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC LHOPKJWDEUNDJS-UHFFFAOYSA-N 0.000 claims 1
- ITPPWWVLEOYDGA-UHFFFAOYSA-N 1-[5-[5-[4-cyclopropyl-3-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F ITPPWWVLEOYDGA-UHFFFAOYSA-N 0.000 claims 1
- MNWDLRMAGWFMGX-UHFFFAOYSA-N 1-[5-[5-[5-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C=1C=C(C=NC=1C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCC1)COC MNWDLRMAGWFMGX-UHFFFAOYSA-N 0.000 claims 1
- GDKAPSYVRUQMST-UHFFFAOYSA-N 1-[5-[5-[5-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C=1C=C(C=NC=1C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCCC1)COC GDKAPSYVRUQMST-UHFFFAOYSA-N 0.000 claims 1
- PGGZYPBZLFAGEV-UHFFFAOYSA-N 1-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(ethoxymethyl)cyclopentyl]methyl-ethylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(CC)CC1(CCCC1)COCC)C(F)(F)F PGGZYPBZLFAGEV-UHFFFAOYSA-N 0.000 claims 1
- CMQNDWSIYJVJEY-UHFFFAOYSA-N 1-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(ethoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-N-methylsulfonylpiperidine-4-carboxamide Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)NS(=O)(=O)C)N(C)CC1(CCCC1)COCC)C(F)(F)F CMQNDWSIYJVJEY-UHFFFAOYSA-N 0.000 claims 1
- VVHIHNCUOOLCND-UHFFFAOYSA-N 1-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCCC1)COC)C(F)(F)F VVHIHNCUOOLCND-UHFFFAOYSA-N 0.000 claims 1
- QOYCQDATNSYSIN-UHFFFAOYSA-N 1-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F QOYCQDATNSYSIN-UHFFFAOYSA-N 0.000 claims 1
- LWMCBUIPOFHVBL-UHFFFAOYSA-N 1-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC(COC)(C)C)C(F)(F)F LWMCBUIPOFHVBL-UHFFFAOYSA-N 0.000 claims 1
- MIDYKOSTIIUBTK-UHFFFAOYSA-N 1-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F MIDYKOSTIIUBTK-UHFFFAOYSA-N 0.000 claims 1
- UVVKCQPOIHHEEZ-UHFFFAOYSA-N 1-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCCC1)COC)C(F)(F)F UVVKCQPOIHHEEZ-UHFFFAOYSA-N 0.000 claims 1
- FBTMVWRWPICCGZ-UHFFFAOYSA-N 1-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F FBTMVWRWPICCGZ-UHFFFAOYSA-N 0.000 claims 1
- UXBRQPFLSBVMMS-UHFFFAOYSA-N 1-[5-[7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-5-[4-methoxy-3-(trifluoromethyl)phenyl]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound COCC1(CCC1)CN(C1=C2C(=NC(=C1)C1=CC(=C(C=C1)OC)C(F)(F)F)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)C UXBRQPFLSBVMMS-UHFFFAOYSA-N 0.000 claims 1
- CEBDUGZIRZVSSE-UHFFFAOYSA-N 1-[5-[7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-5-[6-propyl-5-(trifluoromethyl)pyridin-3-yl]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound COCC1(CCC1)CN(C1=C2C(=NC(=C1)C=1C=NC(=C(C=1)C(F)(F)F)CCC)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)C(=O)O)C CEBDUGZIRZVSSE-UHFFFAOYSA-N 0.000 claims 1
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims 1
- XQYYXUDAKLURFV-UHFFFAOYSA-N 2,2-difluoro-3-[[1-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]amino]propanoic acid Chemical compound CN(CC1(CCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CN=C(C=N4)N5CCC(CC5)NCC(C(=O)O)(F)F)C6=CC(=CC(=C6)F)C(F)(F)F XQYYXUDAKLURFV-UHFFFAOYSA-N 0.000 claims 1
- UXYSVBZRCYRMGK-JOCHJYFZSA-N 2-[(3R)-4-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]acetic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CC(=O)O)C)N(C)CC1(CCCCC1)COC)C(F)(F)F UXYSVBZRCYRMGK-JOCHJYFZSA-N 0.000 claims 1
- JPVZMKSEHOJKSS-LJQANCHMSA-N 2-[(3R)-4-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]acetic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CC(=O)O)C)N(C)CC(COC)(C)C)C(F)(F)F JPVZMKSEHOJKSS-LJQANCHMSA-N 0.000 claims 1
- VNODJGWUGBMQLU-JOCHJYFZSA-N 2-[(3R)-4-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]acetic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CC(=O)O)C)N(C)CC1(CCCCC1)COC)C(F)(F)F VNODJGWUGBMQLU-JOCHJYFZSA-N 0.000 claims 1
- POSQQNFKKGPZPG-GOSISDBHSA-N 2-[(3R)-4-[5-[5-[4-fluoro-3-(trifluoromethyl)phenyl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]acetic acid Chemical compound FC1=C(C=C(C=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CC(=O)O)C)N(C)CC(COC)(C)C)C(F)(F)F POSQQNFKKGPZPG-GOSISDBHSA-N 0.000 claims 1
- VGOMNUNFPXDMHF-LJQANCHMSA-N 2-[(3R)-4-[5-[5-[4-fluoro-3-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]acetic acid Chemical compound FC1=C(C=C(C=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CC(=O)O)C)N(C)CC1(CCC1)COC)C(F)(F)F VGOMNUNFPXDMHF-LJQANCHMSA-N 0.000 claims 1
- KONUUZDAZKDGGJ-HXUWFJFHSA-N 2-[(3R)-4-[5-[5-[4-fluoro-3-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]acetic acid Chemical compound FC1=C(C=C(C=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CC(=O)O)C)N(C)CC1(CCCC1)COC)C(F)(F)F KONUUZDAZKDGGJ-HXUWFJFHSA-N 0.000 claims 1
- KTFSKHXFUWBNDT-JOCHJYFZSA-N 2-[(3R)-4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(ethoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]acetic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CC(=O)O)C)N(C)CC1(CCCC1)COCC)C(F)(F)F KTFSKHXFUWBNDT-JOCHJYFZSA-N 0.000 claims 1
- LEFZELWCAGUUEP-HXUWFJFHSA-N 2-[(3R)-4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]acetic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CC(=O)O)C)N(C)CC1(CCC1)COC)C(F)(F)F LEFZELWCAGUUEP-HXUWFJFHSA-N 0.000 claims 1
- ZFNPTUIBUWAEBW-LJQANCHMSA-N 2-[(3R)-4-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]acetic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CC(=O)O)C)N(C)CC(COC)(C)C)C(F)(F)F ZFNPTUIBUWAEBW-LJQANCHMSA-N 0.000 claims 1
- ISJNURLZVASKGN-HXUWFJFHSA-N 2-[(3R)-4-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]acetic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CC(=O)O)C)N(C)CC1(CCC1)COC)C(F)(F)F ISJNURLZVASKGN-HXUWFJFHSA-N 0.000 claims 1
- GJXAYHDZTMWKOZ-OAQYLSRUSA-N 2-[(3R)-4-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]acetic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CC(=O)O)C)N(C)CC1(CCCC1)COC)C(F)(F)F GJXAYHDZTMWKOZ-OAQYLSRUSA-N 0.000 claims 1
- IXFPOCDBBXKFNK-UHFFFAOYSA-N 2-[1-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidin-4-yl]oxyacetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)OCC(=O)O)N(C)CC1(CCC1)COC IXFPOCDBBXKFNK-UHFFFAOYSA-N 0.000 claims 1
- GTSDSZIMGSINEB-UHFFFAOYSA-N 2-[1-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]oxyacetic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)OCC(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F GTSDSZIMGSINEB-UHFFFAOYSA-N 0.000 claims 1
- IHYXZEMHTRNCSA-UHFFFAOYSA-N 2-[1-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3,3-dimethylpiperidin-4-yl]oxyacetic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CC(C(CC1)OCC(=O)O)(C)C)N(C)CC1(CCCCC1)COC)C(F)(F)F IHYXZEMHTRNCSA-UHFFFAOYSA-N 0.000 claims 1
- PTTUHSUBLLRJIP-UHFFFAOYSA-N 2-[1-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]oxyacetic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)OCC(=O)O)N(C)CC1(CCCCC1)COC)C(F)(F)F PTTUHSUBLLRJIP-UHFFFAOYSA-N 0.000 claims 1
- PFXMSXOMSMTFTE-UHFFFAOYSA-N 2-[1-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3,3-dimethylpiperidin-4-yl]oxyacetic acid Chemical compound CC1(CN(CCC1OCC(=O)O)C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=NC(=C5)C(F)(F)F)C6CC6)N(C)CC7(CCCC7)COC)C PFXMSXOMSMTFTE-UHFFFAOYSA-N 0.000 claims 1
- PKXXCVKZPSQHKS-UHFFFAOYSA-N 2-[1-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-4-methylpiperidin-4-yl]oxyacetic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)(C)OCC(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F PKXXCVKZPSQHKS-UHFFFAOYSA-N 0.000 claims 1
- FOWSALCPPFYQMY-UHFFFAOYSA-N 2-[1-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]sulfanylacetic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CN=C(C=N4)N5CCC(CC5)SCC(=O)O)C6=CC(=NC(=C6)C(F)(F)F)C7CC7 FOWSALCPPFYQMY-UHFFFAOYSA-N 0.000 claims 1
- UXOPAKUAMODQNA-UHFFFAOYSA-N 2-[1-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]sulfanylacetic acid Chemical compound CCOC1=CC(=CC(=N1)C(F)(F)F)C2=NC3=C(C(=C2)N(C)CC4(CCC4)COC)NC(=N3)C5=CN=C(C=N5)N6CCC(CC6)SCC(=O)O UXOPAKUAMODQNA-UHFFFAOYSA-N 0.000 claims 1
- VHPFPIUAMBNQAM-UHFFFAOYSA-N 2-[1-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]oxyacetic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)OCC(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F VHPFPIUAMBNQAM-UHFFFAOYSA-N 0.000 claims 1
- UFXPTIOIHBDVKP-UHFFFAOYSA-N 2-[1-[5-[5-[4-fluoro-3-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]oxyacetic acid Chemical compound FC1=C(C=C(C=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)OCC(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F UFXPTIOIHBDVKP-UHFFFAOYSA-N 0.000 claims 1
- PGSXZWIPHYQZJW-UHFFFAOYSA-N 2-[1-[5-[5-[5-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]oxyacetic acid Chemical compound C1(CC1)C=1C=C(C=NC=1C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)OCC(=O)O)N(C)CC1(CCCC1)COC PGSXZWIPHYQZJW-UHFFFAOYSA-N 0.000 claims 1
- FLGATFHPPAPJAB-UHFFFAOYSA-N 2-[1-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]oxyacetic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)OCC(=O)O)N(C)CC(COC)(C)C)C(F)(F)F FLGATFHPPAPJAB-UHFFFAOYSA-N 0.000 claims 1
- YAEZAOUKXVBZMK-UHFFFAOYSA-N 2-[1-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]oxyacetic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)OCC(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F YAEZAOUKXVBZMK-UHFFFAOYSA-N 0.000 claims 1
- UVRYZGSZRYTNEV-UHFFFAOYSA-N 2-[1-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]oxyacetic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)OCC(=O)O)N(C)CC(COC)(C)C)C(F)(F)F UVRYZGSZRYTNEV-UHFFFAOYSA-N 0.000 claims 1
- AOTABTXFKMCZER-UHFFFAOYSA-N 2-[1-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-4-methylpiperidin-4-yl]oxyacetic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)(C)OCC(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F AOTABTXFKMCZER-UHFFFAOYSA-N 0.000 claims 1
- SDLOSAWYOMKDFO-UHFFFAOYSA-N 2-[1-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]oxyacetic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)OCC(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F SDLOSAWYOMKDFO-UHFFFAOYSA-N 0.000 claims 1
- UIKGLSPJHRDLMT-UHFFFAOYSA-N 2-[1-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]oxyacetic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)OCC(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F UIKGLSPJHRDLMT-UHFFFAOYSA-N 0.000 claims 1
- VUDPYRONVMHJPP-UHFFFAOYSA-N 2-[4-[1-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]ethyl]piperazin-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)C(C)N1CCN(CC1)CC(=O)O)N(C)CC1(CCC1)COC VUDPYRONVMHJPP-UHFFFAOYSA-N 0.000 claims 1
- SJCFHQZRGDONBD-UHFFFAOYSA-N 2-[4-[3-chloro-4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]piperidin-1-yl]acetic acid Chemical compound ClC=1C=C(OC2CCN(CC2)CC(=O)O)C=CC=1C=1NC=2C(=NC(=CC=2N(C)CC2(CCCC2)COC)C=2C=NC(=C(C=2)C(F)(F)F)C2CC2)N=1 SJCFHQZRGDONBD-UHFFFAOYSA-N 0.000 claims 1
- KZJDKNWVBLYPHB-UHFFFAOYSA-N 2-[4-[4-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]piperidin-1-yl]acetic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(OC2CCN(CC2)CC(=O)O)C=C1)N(C)CC1(CCC1)COC)C(F)(F)F KZJDKNWVBLYPHB-UHFFFAOYSA-N 0.000 claims 1
- LPRVDEUZZFCJJQ-UHFFFAOYSA-N 2-[4-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]benzoyl]piperazin-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C(=O)N2CCN(CC2)CC(=O)O)C=C1)N(C)CC1(CCC1)COC LPRVDEUZZFCJJQ-UHFFFAOYSA-N 0.000 claims 1
- DBDOVVKPNHHTJT-UHFFFAOYSA-N 2-[4-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]piperidin-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(OC2CCN(CC2)CC(=O)O)C=C1)N(C)CC1(CCC1)COC DBDOVVKPNHHTJT-UHFFFAOYSA-N 0.000 claims 1
- FEBWMFHFTWPOQY-UHFFFAOYSA-N 2-[4-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-4-hydroxypiperidin-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)C1(CCN(CC1)CC(=O)O)O)N(C)CC1(CCC1)COC FEBWMFHFTWPOQY-UHFFFAOYSA-N 0.000 claims 1
- KHQZMFGLKHMKPU-UHFFFAOYSA-N 2-[4-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperazin-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCN(CC1)CC(=O)O)N(C)CC1(CCC1)COC KHQZMFGLKHMKPU-UHFFFAOYSA-N 0.000 claims 1
- UZQCAPFHOPVSCR-UHFFFAOYSA-N 2-[4-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperazin-1-yl]propanoic acid Chemical compound FC=1C=C(C=C(C1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C2=CC=C(C=C2)N2CCN(CC2)C(C(=O)O)C)N(C)CC2(CCC2)COC UZQCAPFHOPVSCR-UHFFFAOYSA-N 0.000 claims 1
- XQAHVIOVBIDSOF-UHFFFAOYSA-N 2-[4-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidin-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)C1CCN(CC1)CC(=O)O)N(C)CC1(CCC1)COC XQAHVIOVBIDSOF-UHFFFAOYSA-N 0.000 claims 1
- CSZFNYLPWUTHRZ-UHFFFAOYSA-N 2-[4-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-fluorophenoxy]piperidin-1-yl]acetic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=C(C=C(OC2CCN(CC2)CC(=O)O)C=C1)F)N(C)CC1(CCCC1)COC)C(F)(F)F CSZFNYLPWUTHRZ-UHFFFAOYSA-N 0.000 claims 1
- MFQQCTOASHFICS-UHFFFAOYSA-N 2-[4-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]piperidin-1-yl]acetic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(OC2CCN(CC2)CC(=O)O)C=C1)N(C)CC1(CCCC1)COC)C(F)(F)F MFQQCTOASHFICS-UHFFFAOYSA-N 0.000 claims 1
- NKQOXVYUUDERDC-UHFFFAOYSA-N 2-[4-[4-[7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-5-[5-(trifluoromethyl)pyridin-3-yl]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperazin-1-yl]acetic acid Chemical compound COCC1(CCC1)CN(C1=C2C(=NC(=C1)C=1C=NC=C(C=1)C(F)(F)F)N=C(N2)C1=CC=C(C=C1)N1CCN(CC1)CC(=O)O)C NKQOXVYUUDERDC-UHFFFAOYSA-N 0.000 claims 1
- RCXRASQALFHVGQ-UHFFFAOYSA-N 2-[4-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]sulfonylacetic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)S(=O)(=O)CC(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F RCXRASQALFHVGQ-UHFFFAOYSA-N 0.000 claims 1
- DRNLXBKXJPUVAT-UHFFFAOYSA-N 2-[4-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-1,4-diazepan-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CCC1)CC(=O)O)N(C)CC(COC)(C)C DRNLXBKXJPUVAT-UHFFFAOYSA-N 0.000 claims 1
- DZWYPLDBGULGHT-UHFFFAOYSA-N 2-[4-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-1,4-diazepan-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CCC1)CC(=O)O)N(C)CC1(CCC1)COC DZWYPLDBGULGHT-UHFFFAOYSA-N 0.000 claims 1
- LUZLBVCCJGLSAY-UHFFFAOYSA-N 2-[4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-fluoropyridin-2-yl]piperazin-1-yl]acetic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1C=C(C(=NC=1)N1CCN(CC1)CC(=O)O)F)N(C)CC1(CCCC1)COC)C(F)(F)F LUZLBVCCJGLSAY-UHFFFAOYSA-N 0.000 claims 1
- XOSOIVAKFPHFNM-UHFFFAOYSA-N 2-[4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-1,4-diazepan-1-yl]acetic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CCC1)CC(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F XOSOIVAKFPHFNM-UHFFFAOYSA-N 0.000 claims 1
- HDZPICPSXZRTNK-UHFFFAOYSA-N 2-[4-[6-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyridin-3-yl]-1,4-diazepan-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=N1)N1CCN(CCC1)CC(=O)O)N(C)CC1(CCC1)COC HDZPICPSXZRTNK-UHFFFAOYSA-N 0.000 claims 1
- PNNWPKNMMNFUBJ-UHFFFAOYSA-N 2-[4-[6-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyridin-3-yl]piperazin-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=N1)N1CCN(CC1)CC(=O)O)N(C)CC1(CCC1)COC PNNWPKNMMNFUBJ-UHFFFAOYSA-N 0.000 claims 1
- JWVMZAQNMVRXQN-UHFFFAOYSA-N 2-[4-[[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)CN1CCN(CC1)CC(=O)O)N(C)CC1(CCC1)COC JWVMZAQNMVRXQN-UHFFFAOYSA-N 0.000 claims 1
- IWBKNOLIZPRZHW-UHFFFAOYSA-N 2-[[1-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidin-4-yl]-methylamino]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)N(CC(=O)O)C)N(C)CC1(CCC1)COC IWBKNOLIZPRZHW-UHFFFAOYSA-N 0.000 claims 1
- ILLCYEGKKQLPJM-UHFFFAOYSA-N 2-[[1-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidin-4-yl]amino]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)NCC(=O)O)N(C)CC1(CCC1)COC ILLCYEGKKQLPJM-UHFFFAOYSA-N 0.000 claims 1
- AHIJRXMBLULXAV-UHFFFAOYSA-N 2-[[1-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidin-4-yl]amino]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCC(CC1)NCC(=O)O)N(C)CC1(CCC1)COC AHIJRXMBLULXAV-UHFFFAOYSA-N 0.000 claims 1
- YTBWWYXCLMWUSU-HXUWFJFHSA-N 3-[(2R)-4-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@@H]1CN(CCN1CCC(=O)O)C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=NC(=C5)C(F)(F)F)C6CC6)N(C)CC(C)(C)COC YTBWWYXCLMWUSU-HXUWFJFHSA-N 0.000 claims 1
- RUEUHQDSOWRLPE-OAQYLSRUSA-N 3-[(2R)-4-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@@H]1CN(CCN1CCC(=O)O)C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=NC(=C5)C(F)(F)F)C6CC6)N(C)CC7(CCC7)COC RUEUHQDSOWRLPE-OAQYLSRUSA-N 0.000 claims 1
- XVHRESVVALUBJS-HXUWFJFHSA-N 3-[(2R)-4-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=CC(=CC(=N1)C(F)(F)F)C2=NC3=C(C(=C2)N(C)CC(C)(C)COC)NC(=N3)C4=CN=C(C=N4)N5CCN([C@@H](C5)C)CCC(=O)O XVHRESVVALUBJS-HXUWFJFHSA-N 0.000 claims 1
- RBJWTOGSAVQMAB-OAQYLSRUSA-N 3-[(2R)-4-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=CC(=CC(=N1)C(F)(F)F)C2=NC3=C(C(=C2)N(C)CC4(CCC4)COC)NC(=N3)C5=CN=C(C=N5)N6CCN([C@@H](C6)C)CCC(=O)O RBJWTOGSAVQMAB-OAQYLSRUSA-N 0.000 claims 1
- AYQYAHZDUVNMHY-JOCHJYFZSA-N 3-[(2R)-4-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=CC(=CC(=N1)C(F)(F)F)C2=NC3=C(C(=C2)N(C)CC4(CCCC4)COC)NC(=N3)C5=CN=C(C=N5)N6CCN([C@@H](C6)C)CCC(=O)O AYQYAHZDUVNMHY-JOCHJYFZSA-N 0.000 claims 1
- CEPKZSFOGZCVQM-JOCHJYFZSA-N 3-[(2R)-4-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=C(C=C(C=N1)C2=NC3=C(C(=C2)N(C)CC4(CCCC4)COC)NC(=N3)C5=CN=C(C=N5)N6CCN([C@@H](C6)C)CCC(=O)O)C(F)(F)F CEPKZSFOGZCVQM-JOCHJYFZSA-N 0.000 claims 1
- YTTANRFYTKYQCM-FQEVSTJZSA-N 3-[(2S)-4-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1C[C@@H](N(CC1)CCC(=O)O)C)N(C)CC1(CCC1)COC YTTANRFYTKYQCM-FQEVSTJZSA-N 0.000 claims 1
- LPIBNTDEIIUOMF-IBGZPJMESA-N 3-[(2S)-4-[5-[5-[4-fluoro-3-(trifluoromethyl)phenyl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@H]1CN(CCN1CCC(=O)O)C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=C(C=C5)F)C(F)(F)F)N(C)CC(C)(C)COC LPIBNTDEIIUOMF-IBGZPJMESA-N 0.000 claims 1
- ATWLOXDUEOBKMB-FQEVSTJZSA-N 3-[(2S)-4-[5-[5-[4-fluoro-3-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound FC1=C(C=C(C=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1C[C@@H](N(CC1)CCC(=O)O)C)N(C)CC1(CCC1)COC)C(F)(F)F ATWLOXDUEOBKMB-FQEVSTJZSA-N 0.000 claims 1
- NGYSTYSFPGHRRV-FQEVSTJZSA-N 3-[(2S)-4-[5-[5-[5,6-bis(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@H]1CN(CCN1CCC(=O)O)C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=C(N=C5)C(F)(F)F)C(F)(F)F)N(C)CC6(CCCC6)COC NGYSTYSFPGHRRV-FQEVSTJZSA-N 0.000 claims 1
- VGLAVUNKKNWDDB-FQEVSTJZSA-N 3-[(2S)-4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@H]1CN(CCN1CCC(=O)O)C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=C(N=C5)C6CC6)C(F)(F)F)N(C)CC(C)(C)COC VGLAVUNKKNWDDB-FQEVSTJZSA-N 0.000 claims 1
- GNBXHWVWJYCRHB-FQEVSTJZSA-N 3-[(2S)-4-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=C(C=C(C=N1)C2=NC3=C(C(=C2)N(C)CC(C)(C)COC)NC(=N3)C4=CN=C(C=N4)N5CCN([C@H](C5)C)CCC(=O)O)C(F)(F)F GNBXHWVWJYCRHB-FQEVSTJZSA-N 0.000 claims 1
- YHMFSYNEVHLQGF-NRFANRHFSA-N 3-[(2S)-4-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1C[C@@H](N(CC1)CCC(=O)O)C)N(C)CC1(CCC1)COC)C(F)(F)F YHMFSYNEVHLQGF-NRFANRHFSA-N 0.000 claims 1
- ANGWKRMWXFPRCO-OYRHEFFESA-N 3-[(2S,6R)-4-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2,6-dimethylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=CC(=CC(=N1)C(F)(F)F)C2=NC3=C(C(=C2)N(C)CC(C)(C)COC)NC(=N3)C4=CN=C(C=N4)N5C[C@H](N([C@H](C5)C)CCC(=O)O)C ANGWKRMWXFPRCO-OYRHEFFESA-N 0.000 claims 1
- CQYCNOJJSWBLSO-SZPZYZBQSA-N 3-[(2S,6R)-4-[5-[5-[3,5-bis(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2,6-dimethylpiperazin-1-yl]propanoic acid Chemical compound C[C@@H]1CN(C[C@@H](N1CCC(=O)O)C)C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=CC(=C5)C(F)(F)F)C(F)(F)F)N(C)CC6(CCCC6)COC CQYCNOJJSWBLSO-SZPZYZBQSA-N 0.000 claims 1
- MSZSFTWBHPZZPL-RUZDIDTESA-N 3-[(3R)-4-[4-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=CC(=CC(=N1)C(F)(F)F)C2=NC3=C(C(=C2)N(C)CC4(CCCCC4)COC)NC(=N3)C5=CC=C(C=C5)N6CCN(C[C@H]6C)CCC(=O)O MSZSFTWBHPZZPL-RUZDIDTESA-N 0.000 claims 1
- LUMBQSYAUVJJEX-RUZDIDTESA-N 3-[(3R)-4-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@@H]1CN(CCN1C2=CC=C(C=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=C(N=C5)C6CC6)C(F)(F)F)N(C)CC7(CCCCC7)COC)CCC(=O)O LUMBQSYAUVJJEX-RUZDIDTESA-N 0.000 claims 1
- MRXZGIDHRBJCPO-HXUWFJFHSA-N 3-[(3R)-4-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@@H]1CN(CCN1C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=NC(=C5)C(F)(F)F)C6CC6)N(C)CC(C)(C)COC)CCC(=O)O MRXZGIDHRBJCPO-HXUWFJFHSA-N 0.000 claims 1
- KPEFXHMGAPDQIR-OAQYLSRUSA-N 3-[(3R)-4-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@@H]1CN(CCN1C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=NC(=C5)C(F)(F)F)C6CC6)N(C)CC7(CCC7)COC)CCC(=O)O KPEFXHMGAPDQIR-OAQYLSRUSA-N 0.000 claims 1
- XKZQCCRHZBFSSK-HSZRJFAPSA-N 3-[(3R)-4-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CCC(=O)O)C)N(C)CC1(CCCCC1)COC)C(F)(F)F XKZQCCRHZBFSSK-HSZRJFAPSA-N 0.000 claims 1
- QVMADRGWUWSJTI-HXUWFJFHSA-N 3-[(3R)-4-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=CC(=CC(=N1)C(F)(F)F)C2=NC3=C(C(=C2)N(C)CC(C)(C)COC)NC(=N3)C4=CN=C(C=N4)N5CCN(C[C@H]5C)CCC(=O)O QVMADRGWUWSJTI-HXUWFJFHSA-N 0.000 claims 1
- FYWAFFZVUMTBRV-OAQYLSRUSA-N 3-[(3R)-4-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=CC(=CC(=N1)C(F)(F)F)C2=NC3=C(C(=C2)N(C)CC4(CCC4)COC)NC(=N3)C5=CN=C(C=N5)N6CCN(C[C@H]6C)CCC(=O)O FYWAFFZVUMTBRV-OAQYLSRUSA-N 0.000 claims 1
- JVVYUWWEZPMWOS-JOCHJYFZSA-N 3-[(3R)-4-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=CC(=CC(=N1)C(F)(F)F)C2=NC3=C(C(=C2)N(C)CC4(CCCC4)COC)NC(=N3)C5=CN=C(C=N5)N6CCN(C[C@H]6C)CCC(=O)O JVVYUWWEZPMWOS-JOCHJYFZSA-N 0.000 claims 1
- PYKDVDNDMILXQS-LJQANCHMSA-N 3-[(3R)-4-[5-[5-[4-fluoro-3-(trifluoromethyl)phenyl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@@H]1CN(CCN1C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=C(C=C5)F)C(F)(F)F)N(C)CC(C)(C)COC)CCC(=O)O PYKDVDNDMILXQS-LJQANCHMSA-N 0.000 claims 1
- NRMPNLZYEGVOGR-OAQYLSRUSA-N 3-[(3R)-4-[5-[5-[4-fluoro-3-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@@H]1CN(CCN1C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=C(C=C5)F)C(F)(F)F)N(C)CC6(CCCC6)COC)CCC(=O)O NRMPNLZYEGVOGR-OAQYLSRUSA-N 0.000 claims 1
- ZFYYUDYRGKPDEU-HXUWFJFHSA-N 3-[(3R)-4-[5-[5-[5,6-bis(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@@H]1CN(CCN1C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=C(N=C5)C(F)(F)F)C(F)(F)F)N(C)CC6(CCCC6)COC)CCC(=O)O ZFYYUDYRGKPDEU-HXUWFJFHSA-N 0.000 claims 1
- PWLYWEOWXSUDQR-HSZRJFAPSA-N 3-[(3R)-4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(ethoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CCC(=O)O)C)N(C)CC1(CCCC1)COCC)C(F)(F)F PWLYWEOWXSUDQR-HSZRJFAPSA-N 0.000 claims 1
- UOQVELLVYOZMAJ-HSZRJFAPSA-N 3-[(3R)-4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1[C@@H](CN(CC1)CCC(=O)O)C)N(C)CC1(CCCCC1)COC)C(F)(F)F UOQVELLVYOZMAJ-HSZRJFAPSA-N 0.000 claims 1
- DYKZPJVAHMGRLL-HSZRJFAPSA-N 3-[(3R)-4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[ethyl-[[1-(methoxymethyl)cyclopentyl]methyl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound CCN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CN=C(C=N4)N5CCN(C[C@H]5C)CCC(=O)O)C6=CC(=C(N=C6)C7CC7)C(F)(F)F DYKZPJVAHMGRLL-HSZRJFAPSA-N 0.000 claims 1
- BPHQTKCPMIOQRH-OAQYLSRUSA-N 3-[(3R)-4-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=C(C=C(C=N1)C2=NC3=C(C(=C2)N(C)CC4(CCC4)COC)NC(=N3)C5=CN=C(C=N5)N6CCN(C[C@H]6C)CCC(=O)O)C(F)(F)F BPHQTKCPMIOQRH-OAQYLSRUSA-N 0.000 claims 1
- MHOZOZGIZNZSHU-UHFFFAOYSA-N 3-[4-[4-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CC=C(C=C4)N5CCN(CC5)CCC(=O)O)C6=CC(=NC(=C6)C(F)(F)F)C7CC7 MHOZOZGIZNZSHU-UHFFFAOYSA-N 0.000 claims 1
- UFULAVIGCMPNPP-UHFFFAOYSA-N 3-[4-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]piperidin-1-yl]propanoic acid Chemical compound CN(CC1(CCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CC=C(C=C4)OC5CCN(CC5)CCC(=O)O)C6=CC(=CC(=C6)F)C(F)(F)F UFULAVIGCMPNPP-UHFFFAOYSA-N 0.000 claims 1
- CDVZTUJUJQBALO-UHFFFAOYSA-N 3-[4-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidin-1-yl]propanoic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)C1CCN(CC1)CCC(=O)O)N(C)CC1(CCC1)COC CDVZTUJUJQBALO-UHFFFAOYSA-N 0.000 claims 1
- PQBVYLFOFICLCQ-UHFFFAOYSA-N 3-[4-[4-[5-[4-fluoro-3-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CC=C(C=C4)N5CCN(CC5)CCC(=O)O)C6=CC(=C(C=C6)F)C(F)(F)F PQBVYLFOFICLCQ-UHFFFAOYSA-N 0.000 claims 1
- MKXNMRLSNJQSRQ-UHFFFAOYSA-N 3-[4-[4-[5-[5,6-bis(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CC=C(C=C4)N5CCN(CC5)CCC(=O)O)C6=CC(=C(N=C6)C(F)(F)F)C(F)(F)F MKXNMRLSNJQSRQ-UHFFFAOYSA-N 0.000 claims 1
- ZHAQFXNJDGTJRV-UHFFFAOYSA-N 3-[4-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperazin-1-yl]propanoic acid Chemical compound CC(C)(CN(C)C1=CC(=NC2=C1NC(=N2)C3=CC=C(C=C3)N4CCN(CC4)CCC(=O)O)C5=CC(=C(N=C5)C6CC6)C(F)(F)F)COC ZHAQFXNJDGTJRV-UHFFFAOYSA-N 0.000 claims 1
- IMOQTLSXGRDVQA-UHFFFAOYSA-N 3-[4-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CC=C(C=C4)N5CCN(CC5)CCC(=O)O)C6=CC(=C(N=C6)C7CC7)C(F)(F)F IMOQTLSXGRDVQA-UHFFFAOYSA-N 0.000 claims 1
- LIQJCMCVASHURE-UHFFFAOYSA-N 3-[4-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]piperidin-1-yl]propanoic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CC=C(C=C4)OC5CCN(CC5)CCC(=O)O)C6=CC(=C(N=C6)C7CC7)C(F)(F)F LIQJCMCVASHURE-UHFFFAOYSA-N 0.000 claims 1
- BKOBRRMVTUTHES-UHFFFAOYSA-N 3-[4-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CC=C(C=C4)N5CCN(CC5)CCC(=O)O)C6=CC(=C(N=C6)C7CC7)C(F)(F)F BKOBRRMVTUTHES-UHFFFAOYSA-N 0.000 claims 1
- LHLSZZFIAXWMAN-UHFFFAOYSA-N 3-[4-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperazin-1-yl]propanoic acid Chemical compound CCOC1=C(C=C(C=N1)C2=NC3=C(C(=C2)N(C)CC(C)(C)COC)NC(=N3)C4=CC=C(C=C4)N5CCN(CC5)CCC(=O)O)C(F)(F)F LHLSZZFIAXWMAN-UHFFFAOYSA-N 0.000 claims 1
- BQOVUPXMCQOTIM-UHFFFAOYSA-N 3-[4-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperazin-1-yl]propanoic acid Chemical compound CCOC1=C(C=C(C=N1)C2=NC3=C(C(=C2)N(C)CC4(CCCCC4)COC)NC(=N3)C5=CC=C(C=C5)N6CCN(CC6)CCC(=O)O)C(F)(F)F BQOVUPXMCQOTIM-UHFFFAOYSA-N 0.000 claims 1
- ZMMWJMGMBLEOPE-UHFFFAOYSA-N 3-[4-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]butanoic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)C(CC(=O)O)C)N(C)CC1(CCC1)COC)C(F)(F)F ZMMWJMGMBLEOPE-UHFFFAOYSA-N 0.000 claims 1
- VYTCUSBLDITDBM-UHFFFAOYSA-N 3-[4-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CN=C(C=N4)N5CCN(CC5)CCC(=O)O)C6=CC(=NC(=C6)C(F)(F)F)C7CC7 VYTCUSBLDITDBM-UHFFFAOYSA-N 0.000 claims 1
- QNASYOHHFFIKBY-UHFFFAOYSA-N 3-[4-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2,2-dimethylpiperazin-1-yl]propanoic acid Chemical compound CC1(CN(CCN1CCC(=O)O)C2=NC=C(N=C2)C3=NC4=C(N3)C(=CC(=N4)C5=CC(=NC(=C5)C(F)(F)F)C6CC6)N(C)CC7(CCCC7)COC)C QNASYOHHFFIKBY-UHFFFAOYSA-N 0.000 claims 1
- GBXSOKVFJKWNLI-UHFFFAOYSA-N 3-[4-[5-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CN=C(C=N4)N5CCN(CC5)CCC(=O)O)C6=CC(=NC(=C6)C(F)(F)F)C7CC7 GBXSOKVFJKWNLI-UHFFFAOYSA-N 0.000 claims 1
- OPAWPXQHCQBCCW-UHFFFAOYSA-N 3-[4-[5-[5-[2-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)OC1=NC=C(C=C1C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)CCC(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F OPAWPXQHCQBCCW-UHFFFAOYSA-N 0.000 claims 1
- WHLBIXFRHKPJQN-UHFFFAOYSA-N 3-[4-[5-[5-[2-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)OC1=NC=C(C=C1C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)CCC(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F WHLBIXFRHKPJQN-UHFFFAOYSA-N 0.000 claims 1
- ZNJUUHQYESWLKC-UHFFFAOYSA-N 3-[4-[5-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2,2-dimethylpiperazin-1-yl]propanoic acid Chemical compound CCOC1=CC(=CC(=N1)C(F)(F)F)C2=NC3=C(C(=C2)N(C)CC4(CCCC4)COC)NC(=N3)C5=CN=C(C=N5)N6CCN(C(C6)(C)C)CCC(=O)O ZNJUUHQYESWLKC-UHFFFAOYSA-N 0.000 claims 1
- MCBNXGKSEJHDSD-UHFFFAOYSA-N 3-[4-[5-[5-[3,5-bis(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CN=C(C=N4)N5CCN(CC5)CCC(=O)O)C6=CC(=CC(=C6)C(F)(F)F)C(F)(F)F MCBNXGKSEJHDSD-UHFFFAOYSA-N 0.000 claims 1
- FDOHMHSVXBJBMB-UHFFFAOYSA-N 3-[4-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CC(C)(CN(C)C1=CC(=NC2=C1NC(=N2)C3=CN=C(C=N3)N4CCN(CC4)CCC(=O)O)C5=CC(=CC(=C5)F)C(F)(F)F)COC FDOHMHSVXBJBMB-UHFFFAOYSA-N 0.000 claims 1
- GFHIEFGDWAZRPJ-UHFFFAOYSA-N 3-[4-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(2-methoxyethoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)CCC(=O)O)N(C)CC1(CCCC1)COCCOC GFHIEFGDWAZRPJ-UHFFFAOYSA-N 0.000 claims 1
- FCHSMONLLWFDIV-UHFFFAOYSA-N 3-[4-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]-2-oxopiperazin-1-yl]propanoic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CC(N(CC1)CCC(=O)O)=O)N(C)CC1(CCC1)COC FCHSMONLLWFDIV-UHFFFAOYSA-N 0.000 claims 1
- JGDUWQJHLWVZCL-UHFFFAOYSA-N 3-[4-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]butanoic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)C(CC(=O)O)C)N(C)CC1(CCC1)COC JGDUWQJHLWVZCL-UHFFFAOYSA-N 0.000 claims 1
- XLFISYFTCPBUEX-UHFFFAOYSA-N 3-[4-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)CCC(=O)O)N(C)CC1(CCC1)COC XLFISYFTCPBUEX-UHFFFAOYSA-N 0.000 claims 1
- ZPNKGMPVTVXUHY-UHFFFAOYSA-N 3-[4-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyridin-2-yl]-4-hydroxypiperidin-1-yl]propanoic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1C=CC(=NC=1)C1(CCN(CC1)CCC(=O)O)O)N(C)CC1(CCC1)COC ZPNKGMPVTVXUHY-UHFFFAOYSA-N 0.000 claims 1
- CJKDUQBQPKDZQL-UHFFFAOYSA-N 3-[4-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CN=C(C=N4)N5CCN(CC5)CCC(=O)O)C6=CC(=CC(=C6)F)C(F)(F)F CJKDUQBQPKDZQL-UHFFFAOYSA-N 0.000 claims 1
- QTQKIFCEJNOURC-UHFFFAOYSA-N 3-[4-[5-[5-[4-fluoro-3-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CN=C(C=N4)N5CCN(CC5)CCC(=O)O)C6=CC(=C(C=C6)F)C(F)(F)F QTQKIFCEJNOURC-UHFFFAOYSA-N 0.000 claims 1
- SRWUKEXBRBLWDD-UHFFFAOYSA-N 3-[4-[5-[5-[5,6-bis(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CN=C(C=N4)N5CCN(CC5)CCC(=O)O)C6=CC(=C(N=C6)C(F)(F)F)C(F)(F)F SRWUKEXBRBLWDD-UHFFFAOYSA-N 0.000 claims 1
- BZPAWRDQFDMWOL-UHFFFAOYSA-N 3-[4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CC(C)(CN(C)C1=CC(=NC2=C1NC(=N2)C3=CN=C(C=N3)N4CCN(CC4)CCC(=O)O)C5=CC(=C(N=C5)C6CC6)C(F)(F)F)COC BZPAWRDQFDMWOL-UHFFFAOYSA-N 0.000 claims 1
- VTQSRZLXISEDOV-UHFFFAOYSA-N 3-[4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CN=C(C=N4)N5CCN(CC5)CCC(=O)O)C6=CC(=C(N=C6)C7CC7)C(F)(F)F VTQSRZLXISEDOV-UHFFFAOYSA-N 0.000 claims 1
- JQXQBYTWDJRVLZ-UHFFFAOYSA-N 3-[4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-fluoropyridin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=CC(=C(N=C4)N5CCN(CC5)CCC(=O)O)F)C6=CC(=C(N=C6)C7CC7)C(F)(F)F JQXQBYTWDJRVLZ-UHFFFAOYSA-N 0.000 claims 1
- GYYFBWOECIABAJ-UHFFFAOYSA-N 3-[4-[5-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)CCC(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F GYYFBWOECIABAJ-UHFFFAOYSA-N 0.000 claims 1
- RYGOHLSSKXEUIF-UHFFFAOYSA-N 3-[4-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CCOC1=C(C=C(C=N1)C2=NC3=C(C(=C2)N(C)CC(C)(C)COC)NC(=N3)C4=CN=C(C=N4)N5CCN(CC5)CCC(=O)O)C(F)(F)F RYGOHLSSKXEUIF-UHFFFAOYSA-N 0.000 claims 1
- XWTGFBSANRKUAA-UHFFFAOYSA-N 3-[4-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)CCC(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F XWTGFBSANRKUAA-UHFFFAOYSA-N 0.000 claims 1
- WZNOEUJHGXOERV-UHFFFAOYSA-N 3-[4-[5-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)CCC(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F WZNOEUJHGXOERV-UHFFFAOYSA-N 0.000 claims 1
- GELTYLRFUCGVBQ-UHFFFAOYSA-N 3-[4-[5-[7-[[1-(butoxymethyl)cyclopentyl]methyl-methylamino]-5-[3-fluoro-5-(trifluoromethyl)phenyl]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound CCCCOCC1(CCCC1)CN(C)C2=CC(=NC3=C2NC(=N3)C4=CN=C(C=N4)N5CCN(CC5)CCC(=O)O)C6=CC(=CC(=C6)F)C(F)(F)F GELTYLRFUCGVBQ-UHFFFAOYSA-N 0.000 claims 1
- VOUVQQJWORSYGN-UHFFFAOYSA-N 3-[4-[5-[7-[[1-(ethoxymethyl)cyclopentyl]methyl-methylamino]-5-[3-fluoro-5-(trifluoromethyl)phenyl]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)OCC1(CCCC1)CN(C1=C2C(=NC(=C1)C1=CC(=CC(=C1)C(F)(F)F)F)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)CCC(=O)O)C VOUVQQJWORSYGN-UHFFFAOYSA-N 0.000 claims 1
- TZKVEFHKSBXPIO-UHFFFAOYSA-N 3-[4-[6-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyridin-3-yl]piperazin-1-yl]propanoic acid Chemical compound CN(CC1(CCCCC1)COC)C2=CC(=NC3=C2NC(=N3)C4=NC=C(C=C4)N5CCN(CC5)CCC(=O)O)C6=CC(=CC(=C6)F)C(F)(F)F TZKVEFHKSBXPIO-UHFFFAOYSA-N 0.000 claims 1
- JJJLKCQSOLLLJC-UHFFFAOYSA-N 3-[4-fluoro-4-[6-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyridin-3-yl]piperidin-1-yl]propanoic acid Chemical compound FC1(CCN(CC1)CCC(=O)O)C=1C=NC(=CC=1)C=1NC=2C(=NC(=CC=2N(C)CC2(CCC2)COC)C2=CC(=CC(=C2)C(F)(F)F)F)N=1 JJJLKCQSOLLLJC-UHFFFAOYSA-N 0.000 claims 1
- MBXLRMMOQUWSQM-UHFFFAOYSA-N 4-[4-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperazin-1-yl]butanoic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C=1N=CC(=NC=1)N1CCN(CC1)CCCC(=O)O)N(C)CC1(CCC1)COC MBXLRMMOQUWSQM-UHFFFAOYSA-N 0.000 claims 1
- IRPNPHBOANFILX-UHFFFAOYSA-N 4-fluoro-1-[5-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound FC1(CCN(CC1)C1=NC=C(N=C1)C=1NC=2C(=NC(=CC=2N(C)CC2(CCC2)COC)C2=CC(=CC(=C2)C(F)(F)F)F)N=1)C(=O)O IRPNPHBOANFILX-UHFFFAOYSA-N 0.000 claims 1
- YLEDLACPVOVQMR-UHFFFAOYSA-N 4-hydroxy-1-[5-[7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-5-[3-(trifluoromethyl)phenyl]-1H-imidazo[4,5-b]pyridin-2-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound OC1(CCN(CC1)C1=NC=C(N=C1)C=1NC=2C(=NC(=CC=2N(C)CC2(CCC2)COC)C2=CC(=CC=C2)C(F)(F)F)N=1)C(=O)O YLEDLACPVOVQMR-UHFFFAOYSA-N 0.000 claims 1
- NSPAWOCADQULRK-UHFFFAOYSA-N 5-[3-fluoro-5-(trifluoromethyl)phenyl]-N-[[1-(methoxymethyl)cyclobutyl]methyl]-N-methyl-2-[5-[4-(2H-tetrazol-5-yl)piperidin-1-yl]pyrazin-2-yl]-1H-imidazo[4,5-b]pyridin-7-amine Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=NC=C(N=C1)N1CCC(CC1)C1=NN=NN1)N(C)CC1(CCC1)COC NSPAWOCADQULRK-UHFFFAOYSA-N 0.000 claims 1
- SKQGLIOEKRAWAT-UHFFFAOYSA-N 5-[3-fluoro-5-(trifluoromethyl)phenyl]-N-[[1-(methoxymethyl)cyclobutyl]methyl]-N-methyl-2-[5-[4-(2H-tetrazol-5-ylmethyl)piperazin-1-yl]pyrazin-2-yl]-1H-imidazo[4,5-b]pyridin-7-amine Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=NC=C(N=C1)N1CCN(CC1)CC1=NN=NN1)N(C)CC1(CCC1)COC SKQGLIOEKRAWAT-UHFFFAOYSA-N 0.000 claims 1
- QNSGHRCWTUBOQU-UHFFFAOYSA-N 5-[3-fluoro-5-(trifluoromethyl)phenyl]-N-[[1-(methoxymethyl)cyclobutyl]methyl]-N-methyl-2-[5-[4-[2-(2H-tetrazol-5-yl)ethyl]piperazin-1-yl]pyrazin-2-yl]-1H-imidazo[4,5-b]pyridin-7-amine Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=NC=C(N=C1)N1CCN(CC1)CCC1=NN=NN1)N(C)CC1(CCC1)COC QNSGHRCWTUBOQU-UHFFFAOYSA-N 0.000 claims 1
- SCVVOESKIIMTJD-UHFFFAOYSA-N 8-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC2(CC(NC2)=O)CC1)N(C)CC1(CCC1)COC SCVVOESKIIMTJD-UHFFFAOYSA-N 0.000 claims 1
- SKPHEZMSSJBYRP-UHFFFAOYSA-N 8-[4-[7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-5-[3-(trifluoromethyl)phenyl]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid Chemical compound COCC1(CCC1)CN(C1=C2C(=NC(=C1)C1=CC(=CC=C1)C(F)(F)F)N=C(N2)C1=CC=C(C=C1)N1CCC2(CC(=NO2)C(=O)O)CC1)C SKPHEZMSSJBYRP-UHFFFAOYSA-N 0.000 claims 1
- APGFSLJNOJTXSH-UHFFFAOYSA-N 8-[4-[7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-5-[5-(trifluoromethyl)pyridin-3-yl]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid Chemical compound COCC1(CCC1)CN(C1=C2C(=NC(=C1)C=1C=NC=C(C=1)C(F)(F)F)N=C(N2)C1=CC=C(C=C1)N1CCC2(CC(=NO2)C(=O)O)CC1)C APGFSLJNOJTXSH-UHFFFAOYSA-N 0.000 claims 1
- 206010011953 Decreased activity Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010058914 Hypotonic urinary bladder Diseases 0.000 claims 1
- 102000007202 Muscarinic M3 Receptor Human genes 0.000 claims 1
- 108010008405 Muscarinic M3 Receptor Proteins 0.000 claims 1
- 208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims 1
- 206010029279 Neurogenic bladder Diseases 0.000 claims 1
- 208000004168 Underactive Urinary Bladder Diseases 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 210000005070 sphincter Anatomy 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- 210000003708 urethra Anatomy 0.000 claims 1
Classifications
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/396—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having three-membered rings, e.g. aziridine
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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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A—HUMAN NECESSITIES
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
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- A61K31/4965—Non-condensed pyrazines
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- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
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- Ophthalmology & Optometry (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018089867 | 2018-05-08 | ||
| PCT/JP2019/018201 WO2019216294A1 (ja) | 2018-05-08 | 2019-05-07 | アザベンゾイミダゾール化合物及び医薬 |
| EP19800286.7A EP3792260B1 (en) | 2018-05-08 | 2019-05-07 | Azabenzimidazole compounds and pharmaceutical |
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| HRP20241414T1 true HRP20241414T1 (hr) | 2024-12-20 |
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| ES2992256T3 (es) | 2018-05-08 | 2024-12-11 | Nippon Shinyaku Co Ltd | Compuestos de azabencimidazol y producto farmacéutico |
| BR112022008571A2 (pt) | 2019-11-13 | 2022-08-09 | Nippon Shinyaku Co Ltd | Composto de azabenzimidazol e medicamento |
| WO2021095805A1 (ja) * | 2019-11-13 | 2021-05-20 | 日本新薬株式会社 | 機能性消化管障害及び口腔乾燥症の治療剤及び予防剤 |
| CN118045050B (zh) * | 2023-11-16 | 2025-06-10 | 中山大学肿瘤防治中心（中山大学附属肿瘤医院、中山大学肿瘤研究所） | 一种头颈部放疗患者适用的缓解口腔干燥的组合物及其制备方法 |
| WO2025153078A1 (zh) * | 2024-01-17 | 2025-07-24 | 盛睿泽华医药科技（苏州）有限公司 | 可溶性环氧水解酶抑制剂及其应用 |
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| US5571819A (en) | 1994-11-22 | 1996-11-05 | Sabb; Annmarie L. | Imidazopyridines as muscarinic agents |
| NO2005012I1 (no) | 1994-12-28 | 2005-06-06 | Debio Rech Pharma Sa | Triptorelin og farmasoytisk akseptable salter derav |
| UA73543C2 (uk) | 1999-12-07 | 2005-08-15 | Тераванс, Інк. | Похідні сечовини, фармацевтична композиція та застосування похідного при приготуванні лікарського засобу для лікування захворювання, яке опосередковується мускариновим рецептором |
| TW200538095A (en) | 2004-03-11 | 2005-12-01 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
| EP1723142A1 (en) | 2004-03-11 | 2006-11-22 | Theravance, Inc. | Diphenylmethyl compounds useful as muscarinic receptor antagonists |
| EP1734820A4 (en) | 2004-04-16 | 2008-01-23 | Neurogen Corp | Imidazopyrrazine, imidazopyridine, and imidazo-pyrimidine as CRF1 receptor ligands |
| EP1928437A2 (en) | 2005-08-26 | 2008-06-11 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| ES2274712B1 (es) * | 2005-10-06 | 2008-03-01 | Laboratorios Almirall S.A. | Nuevos derivados imidazopiridina. |
| PT2054405E (pt) | 2006-07-11 | 2013-12-24 | Dae Woong Pharma | Novos derivados de biaril benzoimidazol e composição farmacêutica que compreende os mesmos |
| US8008307B2 (en) | 2006-08-08 | 2011-08-30 | Millennium Pharmaceuticals, Inc. | Heteroaryl compounds useful as inhibitors of E1 activating enzymes |
| GB0706168D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| MX2010007587A (es) | 2008-01-24 | 2010-08-04 | Ucb Pharma Sa | Compuestos que comprenden un grupo ciclobutoxi. |
| WO2010130392A1 (de) | 2009-05-11 | 2010-11-18 | Ratiopharm Gmbh | Desfesoterodin in form eines weinsäuresalzes |
| WO2011018894A1 (en) | 2009-08-10 | 2011-02-17 | Raqualia Pharma Inc. | Pyrrolopyrimidine derivatives as potassium channel modulators |
| JP5667934B2 (ja) * | 2010-06-28 | 2015-02-12 | 大日本住友製薬株式会社 | 新規２環性複素環化合物からなる医薬 |
| TWI541243B (zh) | 2010-09-10 | 2016-07-11 | 拜耳知識產權公司 | 經取代咪唑并嗒 |
| CA2821834A1 (en) * | 2010-12-17 | 2012-06-21 | Bayer Intellectual Property Gmbh | 6 substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| JP2013545779A (ja) | 2010-12-17 | 2013-12-26 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 過剰増殖性障害の治療におけるｍｐｓ−１およびｔｋｋ阻害剤として使用するための６置換イミダゾピラジン |
| JP6038150B2 (ja) | 2011-08-24 | 2016-12-07 | ミレニアム ファーマシューティカルズ， インコーポレイテッドＭｉｌｌｅｎｎｉｕｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． | Ｎｅｄｄ８活性化酵素阻害剤 |
| JP2013237634A (ja) | 2012-05-14 | 2013-11-28 | Dainippon Sumitomo Pharma Co Ltd | 縮環イミダゾロン誘導体 |
| GB201302927D0 (en) | 2013-02-20 | 2013-04-03 | Cancer Therapeutics Crc Pty Ltd | Compounds |
| TWI647227B (zh) | 2013-02-28 | 2019-01-11 | 日商安斯泰來製藥股份有限公司 | ２－醯胺噻唑衍生物或其鹽 |
| EA031866B1 (ru) | 2014-06-06 | 2019-03-29 | Астеллас Фарма Инк. | Производное 2-ациламинотиазола или его соль |
| BR112017003901A2 (pt) | 2014-08-26 | 2017-12-12 | Astellas Pharma Inc | derivado de 2-aminotiazola ou sal do mesmo |
| JP6680297B2 (ja) | 2015-04-28 | 2020-04-15 | アステラス製薬株式会社 | 経口投与用医薬組成物 |
| WO2018112840A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6, 5-fused heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| CN115504986B (zh) | 2017-03-03 | 2024-05-14 | 江苏豪森药业集团有限公司 | 凋亡信号调节激酶抑制剂及其制备方法和应用 |
| CA3085745A1 (en) | 2017-12-21 | 2019-06-27 | Kyorin Pharmaceutical Co., Ltd. | An agent for treating nocturnal pollakiuria |
| WO2019189766A1 (ja) | 2018-03-30 | 2019-10-03 | 持田製薬株式会社 | 新規ビアリールアミド誘導体 |
| ES2992256T3 (es) | 2018-05-08 | 2024-12-11 | Nippon Shinyaku Co Ltd | Compuestos de azabencimidazol y producto farmacéutico |
| TW202012415A (zh) | 2018-05-08 | 2020-04-01 | 瑞典商阿斯特捷利康公司 | 化學化合物 |
| WO2021095805A1 (ja) | 2019-11-13 | 2021-05-20 | 日本新薬株式会社 | 機能性消化管障害及び口腔乾燥症の治療剤及び予防剤 |
| BR112022008571A2 (pt) | 2019-11-13 | 2022-08-09 | Nippon Shinyaku Co Ltd | Composto de azabenzimidazol e medicamento |
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