JP2019521167A5 - - Google Patents
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- JP2019521167A5 JP2019521167A5 JP2019502675A JP2019502675A JP2019521167A5 JP 2019521167 A5 JP2019521167 A5 JP 2019521167A5 JP 2019502675 A JP2019502675 A JP 2019502675A JP 2019502675 A JP2019502675 A JP 2019502675A JP 2019521167 A5 JP2019521167 A5 JP 2019521167A5
- Authority
- JP
- Japan
- Prior art keywords
- nicotinamide
- amino
- phenyl
- azabicyclo
- hexan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 152
- 229960003966 nicotinamide Drugs 0.000 claims 76
- 235000005152 nicotinamide Nutrition 0.000 claims 76
- 239000011570 nicotinamide Substances 0.000 claims 76
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 238000006467 substitution reaction Methods 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- -1 optionally N Inorganic materials 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 3
- JRWJZLHBSKAXJW-UHFFFAOYSA-N 2-amino-N-(4-hydroxy-4-methylcyclohexyl)-5-[4-[3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)(C)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C1CCOCC1 JRWJZLHBSKAXJW-UHFFFAOYSA-N 0.000 claims 2
- SRPLSQLPBCVKSL-UHFFFAOYSA-N 2-amino-N-cyclohexyl-5-[4-[2-(4-methylpiperazin-1-yl)ethylcarbamoyl]phenyl]pyridine-3-carboxamide Chemical compound CN1CCN(CCNC(=O)C2=CC=C(C=C2)C2=CN=C(N)C(=C2)C(=O)NC2CCCCC2)CC1 SRPLSQLPBCVKSL-UHFFFAOYSA-N 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 102100034111 Activin receptor type-1 Human genes 0.000 claims 2
- 206010049811 Extraskeletal ossification Diseases 0.000 claims 2
- 206010068715 Fibrodysplasia ossificans progressiva Diseases 0.000 claims 2
- 208000034970 Heterotopic Ossification Diseases 0.000 claims 2
- 101000799140 Homo sapiens Activin receptor type-1 Proteins 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- BAGWVDYVFGYURF-UHFFFAOYSA-N 2-amino-5-(2-fluoro-4-piperazin-1-ylphenyl)-N-(4-hydroxycyclohexyl)pyridine-3-carboxamide Chemical compound NC1=NC=C(C=C1C(=O)NC1CCC(O)CC1)C1=C(F)C=C(C=C1)N1CCNCC1 BAGWVDYVFGYURF-UHFFFAOYSA-N 0.000 claims 1
- MCKAROVXYQRNGJ-UHFFFAOYSA-N 2-amino-5-[2,3-difluoro-4-[(2-methylpyrrolidin-1-yl)methyl]phenyl]-N-(4-hydroxy-4-methylcyclohexyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)(C)O)C=C(C=N1)C1=C(C(=C(C=C1)CN1C(CCC1)C)F)F MCKAROVXYQRNGJ-UHFFFAOYSA-N 0.000 claims 1
- VPYFVDBWVBPVOQ-UHFFFAOYSA-N 2-amino-5-[2-chloro-4-[(2-methylpyrrolidin-1-yl)methyl]phenyl]-N-(4-hydroxy-4-methylcyclohexyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)(C)O)C=C(C=N1)C1=C(C=C(C=C1)CN1C(CCC1)C)Cl VPYFVDBWVBPVOQ-UHFFFAOYSA-N 0.000 claims 1
- IFZOMAMCUJXLIP-UHFFFAOYSA-N 2-amino-5-[2-chloro-4-[1-(2-oxa-6-azaspiro[3.3]heptan-6-yl)ethyl]phenyl]-N-(4-hydroxycyclohexyl)pyridine-3-carboxamide Chemical compound C1OCC11CN(C1)C(C)C1=CC(=C(C=C1)C=1C=NC(=C(C(=O)NC2CCC(CC2)O)C=1)N)Cl IFZOMAMCUJXLIP-UHFFFAOYSA-N 0.000 claims 1
- YPRRJKORYBKLRH-UHFFFAOYSA-N 2-amino-5-[2-fluoro-4-(4-propan-2-ylpiperazin-1-yl)phenyl]-N-(4-hydroxycyclohexyl)pyridine-3-carboxamide Chemical compound CC(C)N1CCN(CC1)C1=CC(F)=C(C=C1)C1=CN=C(N)C(=C1)C(=O)NC1CCC(O)CC1 YPRRJKORYBKLRH-UHFFFAOYSA-N 0.000 claims 1
- XASOXDFSRMCVGS-UHFFFAOYSA-N 2-amino-5-[2-fluoro-4-[(2-methylpyrrolidin-1-yl)methyl]phenyl]-N-(4-hydroxy-4-methylcyclohexyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)(C)O)C=C(C=N1)C1=C(C=C(C=C1)CN1C(CCC1)C)F XASOXDFSRMCVGS-UHFFFAOYSA-N 0.000 claims 1
- FBPYXJFVWDNZCF-UHFFFAOYSA-N 2-amino-5-[3-chloro-4-[(2-methylpyrrolidin-1-yl)methyl]phenyl]-N-(4-hydroxy-4-methylcyclohexyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)(C)O)C=C(C=N1)C1=CC(=C(C=C1)CN1C(CCC1)C)Cl FBPYXJFVWDNZCF-UHFFFAOYSA-N 0.000 claims 1
- VPAYUAUNRWCJTE-UHFFFAOYSA-N 2-amino-5-[4-(2-azaspiro[3.3]heptan-2-ylmethyl)phenyl]-N-(4-hydroxycyclohexyl)pyridine-3-carboxamide Chemical compound C1N(CC11CCC1)CC1=CC=C(C=C1)C=1C=NC(=C(C(=O)NC2CCC(CC2)O)C=1)N VPAYUAUNRWCJTE-UHFFFAOYSA-N 0.000 claims 1
- CCKKGJFQFLRASM-PDXDVJDWSA-N 2-amino-5-[4-[(1R,5S)-3-(2-fluoroethyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)[C@@]12CN(C[C@H]2C1)CCF CCKKGJFQFLRASM-PDXDVJDWSA-N 0.000 claims 1
- RQXROVVCXFAAOM-OCVAFRRMSA-N 2-amino-5-[4-[(1R,5S)-3-(4,4-difluorocyclohexyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)[C@@]12CN(C[C@H]2C1)C1CCC(CC1)(F)F RQXROVVCXFAAOM-OCVAFRRMSA-N 0.000 claims 1
- CCKKGJFQFLRASM-VAMCUKFASA-N 2-amino-5-[4-[(1S,5R)-3-(2-fluoroethyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)pyridine-3-carboxamide Chemical compound Nc1ncc(cc1C(=O)NC12CCC(O)(CC1)CC2)-c1ccc(cc1)[C@]12C[C@H]1CN(CCF)C2 CCKKGJFQFLRASM-VAMCUKFASA-N 0.000 claims 1
- RQXROVVCXFAAOM-GXLPGVSKSA-N 2-amino-5-[4-[(1S,5R)-3-(4,4-difluorocyclohexyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)pyridine-3-carboxamide Chemical compound Nc1ncc(cc1C(=O)NC12CCC(O)(CC1)CC2)-c1ccc(cc1)[C@]12C[C@H]1CN(C2)C1CCC(F)(F)CC1 RQXROVVCXFAAOM-GXLPGVSKSA-N 0.000 claims 1
- ZNGBDCDUILRYET-UHFFFAOYSA-N 2-amino-5-[4-[3-(1,3-difluoropropan-2-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxycyclohexyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C(CF)CF ZNGBDCDUILRYET-UHFFFAOYSA-N 0.000 claims 1
- PBPRYPLWJIJEMD-UHFFFAOYSA-N 2-amino-5-[4-[3-(2,2-difluoropropyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxycyclohexyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)CC(C)(F)F PBPRYPLWJIJEMD-UHFFFAOYSA-N 0.000 claims 1
- JXPPULPLYFLFJI-UHFFFAOYSA-N 2-amino-5-[4-[3-(2-cyanoethyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxycyclohexyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)CCC#N JXPPULPLYFLFJI-UHFFFAOYSA-N 0.000 claims 1
- CCKKGJFQFLRASM-UHFFFAOYSA-N 2-amino-5-[4-[3-(2-fluoroethyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)CCF CCKKGJFQFLRASM-UHFFFAOYSA-N 0.000 claims 1
- MOTRKLJWPDOTBN-UHFFFAOYSA-N 2-amino-5-[4-[3-(2-fluoroethyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxycyclohexyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)CCF MOTRKLJWPDOTBN-UHFFFAOYSA-N 0.000 claims 1
- RQXROVVCXFAAOM-UHFFFAOYSA-N 2-amino-5-[4-[3-(4,4-difluorocyclohexyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C1CCC(CC1)(F)F RQXROVVCXFAAOM-UHFFFAOYSA-N 0.000 claims 1
- NZDLTZYLNOKWBF-UHFFFAOYSA-N 2-amino-5-[4-[3-(4,4-difluorocyclohexyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxy-4-methylcyclohexyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)(C)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C1CCC(CC1)(F)F NZDLTZYLNOKWBF-UHFFFAOYSA-N 0.000 claims 1
- WCTODNJGIAJWJX-UHFFFAOYSA-N 2-amino-5-[4-[3-(4,4-difluorocyclohexyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]-N-(4-hydroxycyclohexyl)pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C1CCC(CC1)(F)F WCTODNJGIAJWJX-UHFFFAOYSA-N 0.000 claims 1
- ODVUZZFWFOPOAH-UHFFFAOYSA-N 2-amino-N-(3-fluoro-4-hydroxycyclohexyl)-5-[4-[3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CC(C(CC2)O)F)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C1CCOCC1 ODVUZZFWFOPOAH-UHFFFAOYSA-N 0.000 claims 1
- QYYWOEFGZQFXCP-UHFFFAOYSA-N 2-amino-N-(3-hydroxy-1-adamantyl)-5-[4-[1-(2-oxa-6-azaspiro[3.3]heptan-6-yl)ethyl]phenyl]pyridine-3-carboxamide Chemical compound C1OCC11CN(C1)C(C)C1=CC=C(C=C1)C=1C=NC(=C(C(=O)NC23CC4(CC(CC(C2)C4)C3)O)C=1)N QYYWOEFGZQFXCP-UHFFFAOYSA-N 0.000 claims 1
- HZFKGEGMOFIQKL-JDANMYFYSA-N 2-amino-N-(4-deuterio-4-hydroxycyclohexyl)-5-[4-(3-propan-2-yl-3-azabicyclo[3.1.0]hexan-1-yl)phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)([2H])O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C(C)C HZFKGEGMOFIQKL-JDANMYFYSA-N 0.000 claims 1
- GAIBPGQSYNAFNN-XSVJXTIASA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[(1R,5S)-3-(2-morpholin-4-ylethyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)[C@@]12CN(C[C@H]2C1)CCN1CCOCC1 GAIBPGQSYNAFNN-XSVJXTIASA-N 0.000 claims 1
- GHUBYLSYFHNRLX-BORAJFNMSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)[C@@]12CN(C[C@H]2C1)C1COC1 GHUBYLSYFHNRLX-BORAJFNMSA-N 0.000 claims 1
- GNDTWZQOAXPKCV-DTHGUCGZSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[(1S,5R)-3-(2-methoxyethyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound COCCN1C[C@@H]2C[C@@]2(C1)c1ccc(cc1)-c1cnc(N)c(c1)C(=O)NC12CCC(O)(CC1)CC2 GNDTWZQOAXPKCV-DTHGUCGZSA-N 0.000 claims 1
- GAIBPGQSYNAFNN-BVPJRLQBSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[(1S,5R)-3-(2-morpholin-4-ylethyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound Nc1ncc(cc1C(=O)NC12CCC(O)(CC1)CC2)-c1ccc(cc1)[C@]12C[C@H]1CN(CCN1CCOCC1)C2 GAIBPGQSYNAFNN-BVPJRLQBSA-N 0.000 claims 1
- GHUBYLSYFHNRLX-ZKSXBLTCSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[(1S,5R)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound Nc1ncc(cc1C(=O)NC12CCC(O)(CC1)CC2)-c1ccc(cc1)[C@]12C[C@H]1CN(C2)C1COC1 GHUBYLSYFHNRLX-ZKSXBLTCSA-N 0.000 claims 1
- GNDTWZQOAXPKCV-UHFFFAOYSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[3-(2-methoxyethyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)CCOC GNDTWZQOAXPKCV-UHFFFAOYSA-N 0.000 claims 1
- GAIBPGQSYNAFNN-UHFFFAOYSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[3-(2-morpholin-4-ylethyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)CCN1CCOCC1 GAIBPGQSYNAFNN-UHFFFAOYSA-N 0.000 claims 1
- KPRPFTOLWQQUAV-UHFFFAOYSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C1CCOCC1 KPRPFTOLWQQUAV-UHFFFAOYSA-N 0.000 claims 1
- VYIZLEBMEIYFLA-UHFFFAOYSA-N 2-amino-N-(4-hydroxy-1-methylcyclohexyl)-5-[4-[1-(2-oxa-6-azaspiro[3.3]heptan-6-yl)ethyl]phenyl]pyridine-3-carboxamide Chemical compound C1OCC11CN(C1)C(C)C1=CC=C(C=C1)C=1C=NC(=C(C(=O)NC2(CCC(CC2)O)C)C=1)N VYIZLEBMEIYFLA-UHFFFAOYSA-N 0.000 claims 1
- DYPKOAOCIPJRSB-UHFFFAOYSA-N 2-amino-N-(4-hydroxy-4-methylcyclohexyl)-5-[2-methyl-4-[(2-methylpyrrolidin-1-yl)methyl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)(C)O)C=C(C=N1)C1=C(C=C(C=C1)CN1C(CCC1)C)C DYPKOAOCIPJRSB-UHFFFAOYSA-N 0.000 claims 1
- DBAUTMSTTOYZCH-UHFFFAOYSA-N 2-amino-N-(4-hydroxy-4-methylcyclohexyl)-5-[4-(3-propan-2-yl-3-azabicyclo[3.1.0]hexan-1-yl)phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)(C)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C(C)C DBAUTMSTTOYZCH-UHFFFAOYSA-N 0.000 claims 1
- JAGKUGSFENQDHG-UHFFFAOYSA-N 2-amino-N-(4-hydroxy-4-methylcyclohexyl)-5-[4-[(2-methylpyrrolidin-1-yl)methyl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)(C)O)C=C(C=N1)C1=CC=C(C=C1)CN1C(CCC1)C JAGKUGSFENQDHG-UHFFFAOYSA-N 0.000 claims 1
- XBGQOGKKOFCYQD-UHFFFAOYSA-N 2-amino-N-(4-hydroxy-4-methylcyclohexyl)-5-[4-[1-(2-oxa-6-azaspiro[3.3]heptan-6-yl)ethyl]phenyl]pyridine-3-carboxamide Chemical compound C1OCC11CN(C1)C(C)C1=CC=C(C=C1)C=1C=NC(=C(C(=O)NC2CCC(CC2)(C)O)C=1)N XBGQOGKKOFCYQD-UHFFFAOYSA-N 0.000 claims 1
- AKSKEXPIRSTUBP-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-(4-pyrrolidin-3-ylphenyl)pyridine-3-carboxamide Chemical compound NC1=NC=C(C=C1C(=O)NC1CCC(O)CC1)C1=CC=C(C=C1)C1CCNC1 AKSKEXPIRSTUBP-UHFFFAOYSA-N 0.000 claims 1
- ZYBANBICDUFKMJ-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-(1-propan-2-ylpyrrolidin-3-yl)phenyl]pyridine-3-carboxamide Chemical compound CC(C)N1CCC(C1)C1=CC=C(C=C1)C1=CN=C(N)C(=C1)C(=O)NC1CCC(O)CC1 ZYBANBICDUFKMJ-UHFFFAOYSA-N 0.000 claims 1
- HZFKGEGMOFIQKL-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-(3-propan-2-yl-3-azabicyclo[3.1.0]hexan-1-yl)phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C(C)C HZFKGEGMOFIQKL-UHFFFAOYSA-N 0.000 claims 1
- ZWIZYDKWXQTSEQ-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-(4-methylpiperazine-1-carbonyl)phenyl]pyridine-3-carboxamide Chemical compound CN1CCN(CC1)C(=O)C1=CC=C(C=C1)C1=CN=C(N)C(=C1)C(=O)NC1CCC(O)CC1 ZWIZYDKWXQTSEQ-UHFFFAOYSA-N 0.000 claims 1
- WTEJOBNHOMFLQN-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-[(2-methylpyrrolidin-1-yl)methyl]phenyl]pyridine-3-carboxamide Chemical compound CC1CCCN1Cc1ccc(cc1)-c1cnc(N)c(c1)C(=O)NC1CCC(O)CC1 WTEJOBNHOMFLQN-UHFFFAOYSA-N 0.000 claims 1
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- JFDSOYMKCLUKEJ-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-[3-(2-morpholin-4-ylethyl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)CCN1CCOCC1 JFDSOYMKCLUKEJ-UHFFFAOYSA-N 0.000 claims 1
- RCORIFCNLQIMKN-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-[3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C1COC1 RCORIFCNLQIMKN-UHFFFAOYSA-N 0.000 claims 1
- IOEZZOIIFUBFFP-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-[3-[2-(2,2,2-trifluoroethoxy)ethyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC2CCC(CC2)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)CCOCC(F)(F)F IOEZZOIIFUBFFP-UHFFFAOYSA-N 0.000 claims 1
- WTEJOBNHOMFLQN-YMTQGWHGSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-[[(2R)-2-methylpyrrolidin-1-yl]methyl]phenyl]pyridine-3-carboxamide Chemical compound C[C@@H]1CCCN1CC1=CC=C(C=C1)C1=CN=C(N)C(=C1)C(=O)NC1CCC(O)CC1 WTEJOBNHOMFLQN-YMTQGWHGSA-N 0.000 claims 1
- UJOAYZNRVRGXPF-SAQMYGGWSA-N 2-amino-N-[3-(2-hydroxypropan-2-yl)-1-bicyclo[1.1.1]pentanyl]-5-[4-[(1R,5S)-3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CC(C2)(C3)C(C)(C)O)C=C(C=N1)C1=CC=C(C=C1)[C@@]12CN(C[C@H]2C1)C1CCOCC1 UJOAYZNRVRGXPF-SAQMYGGWSA-N 0.000 claims 1
- UJOAYZNRVRGXPF-UHFFFAOYSA-N 2-amino-N-[3-(2-hydroxypropan-2-yl)-1-bicyclo[1.1.1]pentanyl]-5-[4-[3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CC(C2)(C3)C(C)(C)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C1CCOCC1 UJOAYZNRVRGXPF-UHFFFAOYSA-N 0.000 claims 1
- WBRIXUZLHYMBMA-UHFFFAOYSA-N 2-amino-N-[3-(hydroxymethyl)-1-bicyclo[1.1.1]pentanyl]-5-[4-(3-propan-2-yl-3-azabicyclo[3.1.0]hexan-1-yl)phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CC(C2)(C3)CO)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C(C)C WBRIXUZLHYMBMA-UHFFFAOYSA-N 0.000 claims 1
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- WBRIXUZLHYMBMA-QQYNMQCVSA-N 2-amino-N-[3-(hydroxymethyl)-1-bicyclo[1.1.1]pentanyl]-5-[4-[(1R,5S)-3-propan-2-yl-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CC(C2)(C3)CO)C=C(C=N1)C1=CC=C(C=C1)[C@@]12CN(C[C@H]2C1)C(C)C WBRIXUZLHYMBMA-QQYNMQCVSA-N 0.000 claims 1
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| WO2018106820A1 (en) | 2016-12-07 | 2018-06-14 | Kura Oncology, Inc. | Methods of promoting beta cell proliferation |
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