JPWO2019216294A5

JPWO2019216294A5 -

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Publication number: JPWO2019216294A5
Authority: JP; Japan
Prior art keywords: methyl; pyridin; imidazo; trifluoromethyl; amino
Prior art date: 2019-05-07
Legal status : Granted

Application number

JP2020518289A

Other languages

English (en)

Japanese (ja)

Other versions

JP7235047B2 (ja

JPWO2019216294A1 (ja

Filing date

2019-05-07

Publication date

2023-01-19

2019-05-07 Application filed filed Critical

2019-05-07 Priority claimed from PCT/JP2019/018201 external-priority patent/WO2019216294A1/ja

2021-05-13 Publication of JPWO2019216294A1 publication Critical patent/JPWO2019216294A1/ja

2023-01-19 Publication of JPWO2019216294A5 publication Critical patent/JPWO2019216294A5/ja

2023-03-08 Application granted granted Critical

2023-03-08 Publication of JP7235047B2 publication Critical patent/JP7235047B2/ja

Status Active legal-status Critical Current

2039-05-07 Anticipated expiration legal-status Critical

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229910052757 nitrogen Inorganic materials 0.000 claims description 32
125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 21
-1 azabenzimidazole compound Chemical class 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
239000012453 solvate Substances 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical group 0.000 claims description 8
125000004385 trihaloalkyl group Chemical group 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
206010013990 dysuria Diseases 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
102000017925 CHRM3 Human genes 0.000 claims description 3
101150060249 CHRM3 gene Proteins 0.000 claims description 3
208000012931 Urologic disease Diseases 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
229940124597 therapeutic agent Drugs 0.000 claims description 3
208000026533 urinary bladder disease Diseases 0.000 claims description 3
208000014001 urinary system disease Diseases 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical group C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 2
102100035102 E3 ubiquitin-protein ligase MYCBP2 Human genes 0.000 claims description 2
208000010412 Glaucoma Diseases 0.000 claims description 2
229910005965 SO 2 Inorganic materials 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
206010012601 diabetes mellitus Diseases 0.000 claims description 2
230000000694 effects Effects 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
230000000069 prophylactic effect Effects 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 27
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 27
235000019260 propionic acid Nutrition 0.000 claims 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 5
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
208000004168 Underactive Urinary Bladder Diseases 0.000 claims 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
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
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
KLTIOSMKFHIZOT-HXUWFJFHSA-N 2-[(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]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(CCC1)COC)C(F)(F)F KLTIOSMKFHIZOT-HXUWFJFHSA-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
BINSMMJCVXYQSQ-JOCHJYFZSA-N 2-[(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]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(CCCCC1)COC)C(F)(F)F BINSMMJCVXYQSQ-JOCHJYFZSA-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
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
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
JWGSKPFSJBLUDN-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]methyl]piperidin-4-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)CN1CCC(CC1)CC(=O)O)N(C)CC1(CCC1)COC JWGSKPFSJBLUDN-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
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
QISJRPGTYCPSOE-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]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)C=1N=CC(=NC=1)N1CCN(CC1)CC(=O)O)N(C)CC1(CCC1)COC QISJRPGTYCPSOE-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
IHTORGBKEIAMBN-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]-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=N1)C1(CCN(CC1)CC(=O)O)O)N(C)CC1(CCC1)COC IHTORGBKEIAMBN-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
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
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
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
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
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
206010003591 Ataxia Diseases 0.000 claims 1
208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims 1
206010029279 Neurogenic bladder Diseases 0.000 claims 1
125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
230000003449 preventive effect Effects 0.000 claims 1
210000005070 sphincter Anatomy 0.000 claims 1
238000000034 method Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
150000002466 imines Chemical class 0.000 description 2
238000006268 reductive amination reaction Methods 0.000 description 2
125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

JP2020518289A 2018-05-08 2019-05-07 アザベンゾイミダゾール化合物及び医薬 Active JP7235047B2 (ja)