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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Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5077290A (en) | 1990-10-11 | 1991-12-31 | Merck & Co., Inc. | Morpholine derivatives compositions and use |
| KR950704485A (ko) | 1992-11-17 | 1995-11-20 | 로이드 제이. 오울드·에드워드 에이, 맥더모 2세 | 액티빈 리셉터-유사 키나제, 세린 트레오닌 키나제 도메인을 갖는 단백질 및 이들의 용도(activin receptor-like kinases, proteins having serine threonine kinase domains and their use) |
| TW530054B (en) | 1997-09-24 | 2003-05-01 | Duphar Int Res | New piperazine and piperidine compounds |
| SE0102439D0 (sv) | 2001-07-05 | 2001-07-05 | Astrazeneca Ab | New compounds |
| US6914058B2 (en) | 2002-01-18 | 2005-07-05 | Dr. Reddy's Laboratories, Limited | Antibacterial compounds: process for their preparation and pharmaceutical compositions containing them |
| WO2003093297A2 (en) | 2002-05-03 | 2003-11-13 | Exelixis, Inc. | Protein kinase modulators and methods of use |
| AU2003249369A1 (en) | 2002-06-21 | 2004-01-06 | Cellular Genomics, Inc. | Certain amino-substituted monocycles as kinase modulators |
| US20040067985A1 (en) | 2002-10-04 | 2004-04-08 | Fortuna Haviv | Method of inhibiting angiogenesis |
| SE0203753D0 (sv) | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
| FR2850652B1 (fr) * | 2003-01-31 | 2008-05-30 | Aventis Pharma Sa | Nouveaux derives d'uree cyclique, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de kinases |
| JP2007524596A (ja) | 2003-02-28 | 2007-08-30 | トランスフォーム・ファーマシューティカルズ・インコーポレイテッド | 共結晶医薬組成物 |
| CA2521766A1 (en) | 2003-04-11 | 2004-10-28 | Sgx Pharmaceuticals, Inc. | Compound libraries and methods for drug discovery |
| EA200601982A1 (ru) | 2004-05-27 | 2007-04-27 | Пфайзер Инк. | Производные аминопиридина в качестве селективных агонистов d3 - дофаминовых рецепторов |
| SA05260265A (ar) | 2004-08-30 | 2005-12-03 | استرازينيكا ايه بي | مركبات جديدة |
| BRPI0607913A2 (pt) | 2005-04-08 | 2010-03-23 | Eisai R&D Man Co Ltd | agente terapÊutico para discinesia |
| WO2007011760A2 (en) | 2005-07-15 | 2007-01-25 | Kalypsys, Inc. | Inhibitors of mitotic kinesin |
| GB0517175D0 (en) | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| PE20071241A1 (es) * | 2006-01-17 | 2008-01-14 | Schering Corp | Compuestos derivados de hidantoina para el tratamiento de trastornos inflamatorios |
| WO2007123896A2 (en) | 2006-04-18 | 2007-11-01 | The Trustees Of The University Of Pennsylvania | Mutated acvr1 for diagnosis and treatment of fibrodyplasia ossificans progressiva (fop) |
| WO2008002671A2 (en) | 2006-06-29 | 2008-01-03 | Alantos Pharmaceuticals Holding, Inc. | Metalloprotease inhibitors |
| EA200970250A1 (ru) | 2006-09-05 | 2010-02-26 | Медарекс, Инк. | Антитела к костным морфогенетическим белкам и их рецепторам и способы их применения |
| WO2008033408A2 (en) | 2006-09-12 | 2008-03-20 | The General Hospital Corporation | Methods for identifying compounds that modulate cell signaling and methods employing such compounds |
| UA97813C2 (uk) * | 2006-12-05 | 2012-03-26 | Янссен Фармацевтика Н.В. | Фумаратна сіль (альфа s, бета r)-6-бром-альфа-[2-(диметиламіно)етил]-2-метоксі-альфа-1-нафталеніл-бета-феніл-3-хінолінетанолу |
| US8507501B2 (en) | 2008-03-13 | 2013-08-13 | The Brigham And Women's Hospital, Inc. | Inhibitors of the BMP signaling pathway |
| US20110294836A1 (en) | 2008-06-20 | 2011-12-01 | Metabolex, Inc. | Aryl gpr119 agonists and uses thereof |
| KR101630501B1 (ko) | 2010-08-20 | 2016-06-15 | 와이어쓰 엘엘씨 | 디자이너 골형성 단백질 |
| CN103402520A (zh) | 2010-12-06 | 2013-11-20 | 皮拉马尔企业有限公司 | 具有取代基的咪唑并喹啉衍生物 |
| WO2012087938A1 (en) | 2010-12-20 | 2012-06-28 | Glaxosmithkline Llc | Quinazolinone derivatives as antiviral agents |
| EP2655334B1 (en) | 2010-12-22 | 2018-10-03 | Eutropics Pharmaceuticals, Inc. | Compositions and methods useful for treating diseases |
| WO2012161877A1 (en) | 2011-05-23 | 2012-11-29 | Merck Patent Gmbh | Pyridine-and pyrazine derivatives |
| CN104159890B (zh) | 2011-09-09 | 2018-04-10 | 蓝瑟斯医学影像公司 | 用于合成和使用显像剂的组合物、方法和系统 |
| CA2886187C (en) * | 2012-09-28 | 2020-04-14 | Vanderbilt University | Fused heterocyclic compounds as selective bmp inhibitors |
| JP2016510745A (ja) * | 2013-03-04 | 2016-04-11 | ザ ブリガム アンド ウィメンズ ホスピタル インコーポレイテッドＴｈｅ Ｂｒｉｇｈａｍ ａｎｄ Ｗｏｍｅｎ’ｓ Ｈｏｓｐｉｔａｌ， Ｉｎｃ． | Ｂｍｐ阻害剤およびその使用方法 |
| US9682983B2 (en) | 2013-03-14 | 2017-06-20 | The Brigham And Women's Hospital, Inc. | BMP inhibitors and methods of use thereof |
| JP6433974B2 (ja) * | 2013-03-14 | 2018-12-05 | トレロ ファーマシューティカルズ， インコーポレイテッド | Ｊａｋ２およびａｌｋ２阻害剤およびその使用方法 |
| EP3060550B1 (en) | 2013-10-21 | 2019-05-15 | Merck Patent GmbH | Heteroaryl compounds as btk inhibitors and uses thereof |
| US10260068B2 (en) | 2014-03-31 | 2019-04-16 | Sumitomo Dainippon Pharma Co., Ltd. | Prophylactic agent and therapeutic agent for fibrodysplasia ossificans progressiva |
| ES2907461T3 (es) | 2015-01-20 | 2022-04-25 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos antihelmínticos, composiciones y procedimientos de uso de los mismos |
| MX387785B (es) | 2015-08-31 | 2025-03-18 | Dong A Socio Holdings Co Ltd | Compuestos heteroarilo y su uso como farmacos terapeuticos. |
| JP7030775B2 (ja) | 2016-07-20 | 2022-03-07 | キャベンディッシュ・キネティックス・インコーポレイテッド | Ｄｖｃを用いてアンテナを調整する方法 |
| PT3971177T (pt) * | 2016-07-20 | 2024-07-30 | Novartis Ag | Derivados de aminopiridina e a sua utilização como inibidores seletivos de alk-2 |
| WO2018106820A1 (en) | 2016-12-07 | 2018-06-14 | Kura Oncology, Inc. | Methods of promoting beta cell proliferation |
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2017
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- 2017-07-18 PL PL21202619.9T patent/PL3971177T3/pl unknown
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2019
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2020
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