FI3971177T3 - Aminopyridiinijohdannaisia ja niiden käyttö selektiivisinä alk-2:n estäjinä - Google Patents
Aminopyridiinijohdannaisia ja niiden käyttö selektiivisinä alk-2:n estäjinä Download PDFInfo
- Publication number
- FI3971177T3 FI3971177T3 FIEP21202619.9T FI21202619T FI3971177T3 FI 3971177 T3 FI3971177 T3 FI 3971177T3 FI 21202619 T FI21202619 T FI 21202619T FI 3971177 T3 FI3971177 T3 FI 3971177T3
- Authority
- FI
- Finland
- Prior art keywords
- nicotinamide
- amino
- phenyl
- azabicyclo
- hexan
- Prior art date
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- 150000003927 aminopyridines Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 140
- 229960003966 nicotinamide Drugs 0.000 claims 70
- 235000005152 nicotinamide Nutrition 0.000 claims 70
- 239000011570 nicotinamide Substances 0.000 claims 70
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000005842 heteroatom Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 229910052717 sulfur Inorganic materials 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 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 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- -1 hydroxyl-substituted bicyclo[2.2.2]octanyl Chemical group 0.000 claims 3
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- JHBVJUXBKKKJGW-UHFFFAOYSA-N 2-amino-N-(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)NC2CCC(CC2)O)C=C(C=N1)C1=CC=C(C=C1)C12CN(CC2C1)C1CCOCC1 JHBVJUXBKKKJGW-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
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 206010068715 Fibrodysplasia ossificans progressiva Diseases 0.000 claims 2
- 208000034970 Heterotopic Ossification Diseases 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 230000007941 heterotopic ossification Effects 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
- BBWFHMVFMVFXJP-UHFFFAOYSA-N 2-amino-5-[4-(3-but-2-ynyl-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#CC BBWFHMVFMVFXJP-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
- 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
- AWERICKZHUFDGO-UHFFFAOYSA-N 2-amino-5-[4-[3-(1,1-dioxothian-4-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)C1CCS(CC1)(=O)=O AWERICKZHUFDGO-UHFFFAOYSA-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
- 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
- KPRPFTOLWQQUAV-OCVAFRRMSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-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)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)[C@@]12CN(C[C@H]2C1)C1CCOCC1 KPRPFTOLWQQUAV-OCVAFRRMSA-N 0.000 claims 1
- JYMHACJJTJNBGE-XESJLZEZSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[(1R,5S)-3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide (E)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.Nc1ncc(cc1C(=O)NC12CCC(O)(CC1)CC2)-c1ccc(cc1)[C@@]12C[C@@H]1CN(C2)C1CCOCC1 JYMHACJJTJNBGE-XESJLZEZSA-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
- KPRPFTOLWQQUAV-GXLPGVSKSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[(1S,5R)-3-(oxan-4-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)C1CCOCC1 KPRPFTOLWQQUAV-GXLPGVSKSA-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
- GHUBYLSYFHNRLX-UHFFFAOYSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[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)C12CN(CC2C1)C1COC1 GHUBYLSYFHNRLX-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
- 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 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
- MKKQYAXMQPGYNY-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-(3-prop-2-ynyl-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)CC#C MKKQYAXMQPGYNY-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
- GPLMXGSESNBQQL-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-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)O)C=1)N GPLMXGSESNBQQL-UHFFFAOYSA-N 0.000 claims 1
- NNGJBTGAVCLGTM-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-[3-(2,2,2-trifluoroethyl)-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)CC(F)(F)F NNGJBTGAVCLGTM-UHFFFAOYSA-N 0.000 claims 1
- NJSRQYMTTJJEJH-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-[3-(2-methoxyethyl)-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)CCOC NJSRQYMTTJJEJH-UHFFFAOYSA-N 0.000 claims 1
- 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
- DONRBWYKHKBNAQ-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-[3-(3,3,3-trifluoropropyl)-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)CCC(F)(F)F DONRBWYKHKBNAQ-UHFFFAOYSA-N 0.000 claims 1
- FCURQEMLQWEPFI-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-[3-(3-morpholin-4-ylpropyl)-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)CCCN1CCOCC1 FCURQEMLQWEPFI-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
- NSVCYZBCJCPLDO-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-[3-(oxetan-3-ylmethyl)-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)CC1COC1 NSVCYZBCJCPLDO-UHFFFAOYSA-N 0.000 claims 1
- TUFWPHNCGNFLJQ-UHFFFAOYSA-N 2-amino-N-(4-hydroxycyclohexyl)-5-[4-[3-[1-(2,2,2-trifluoroethyl)piperidin-4-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)C1CCN(CC1)CC(F)(F)F TUFWPHNCGNFLJQ-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
- ODVUZZFWFOPOAH-JVFDCBABSA-N 2-amino-N-[(1R,3S,4R)-3-fluoro-4-hydroxycyclohexyl]-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)N[C@H]2C[C@@H]([C@@H](CC2)O)F)C=C(C=N1)C1=CC=C(C=C1)[C@@]12CN(C[C@H]2C1)C1CCOCC1 ODVUZZFWFOPOAH-JVFDCBABSA-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
- MEDZXCCPJFWNLJ-BORAJFNMSA-N 2-amino-N-[3-(hydroxymethyl)-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)CO)C=C(C=N1)C1=CC=C(C=C1)[C@@]12CN(C[C@H]2C1)C1CCOCC1 MEDZXCCPJFWNLJ-BORAJFNMSA-N 0.000 claims 1
- 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
- MEDZXCCPJFWNLJ-ZKSXBLTCSA-N 2-amino-N-[3-(hydroxymethyl)-1-bicyclo[1.1.1]pentanyl]-5-[4-[(1S,5R)-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)CO)C=C(C=N1)C1=CC=C(C=C1)[C@]12CN(C[C@@H]2C1)C1CCOCC1 MEDZXCCPJFWNLJ-ZKSXBLTCSA-N 0.000 claims 1
- WBRIXUZLHYMBMA-PMISWQISSA-N 2-amino-N-[3-(hydroxymethyl)-1-bicyclo[1.1.1]pentanyl]-5-[4-[(1S,5R)-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-PMISWQISSA-N 0.000 claims 1
- LDFGETAUTXIODG-UHFFFAOYSA-N 2-amino-N-cyclohexyl-5-(4-morpholin-4-ylphenyl)pyridine-3-carboxamide Chemical compound NC1=NC=C(C=C1C(=O)NC1CCCCC1)C1=CC=C(C=C1)N1CCOCC1 LDFGETAUTXIODG-UHFFFAOYSA-N 0.000 claims 1
- RVRSJCNFHLBUKI-UHFFFAOYSA-N 2-amino-N-cyclohexyl-5-(4-piperidin-1-ylphenyl)pyridine-3-carboxamide Chemical compound NC1=NC=C(C=C1C(=O)NC1CCCCC1)C1=CC=C(C=C1)N1CCCCC1 RVRSJCNFHLBUKI-UHFFFAOYSA-N 0.000 claims 1
- LJYGDHOBWBXZIU-UHFFFAOYSA-N 2-amino-N-cyclohexyl-5-[3-(morpholine-4-carbonyl)phenyl]pyridine-3-carboxamide Chemical compound NC1=NC=C(C=C1C(=O)NC1CCCCC1)C1=CC(=CC=C1)C(=O)N1CCOCC1 LJYGDHOBWBXZIU-UHFFFAOYSA-N 0.000 claims 1
- YPNVOEHUQFQAFV-UHFFFAOYSA-N 2-amino-N-cyclohexyl-5-[3-[4-(2-hydroxyethyl)piperazine-1-carbonyl]phenyl]pyridine-3-carboxamide Chemical compound NC1=NC=C(C=C1C(=O)NC1CCCCC1)C1=CC(=CC=C1)C(=O)N1CCN(CCO)CC1 YPNVOEHUQFQAFV-UHFFFAOYSA-N 0.000 claims 1
- KPONRYYSJPIILR-UHFFFAOYSA-N 2-amino-N-cyclohexyl-5-[4-(3-morpholin-4-ylpropoxy)phenyl]pyridine-3-carboxamide Chemical compound NC1=NC=C(C=C1C(=O)NC1CCCCC1)C1=CC=C(OCCCN2CCOCC2)C=C1 KPONRYYSJPIILR-UHFFFAOYSA-N 0.000 claims 1
- FJHJLNXCFAIWOY-UHFFFAOYSA-N 2-amino-N-cyclohexyl-5-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridine-3-carboxamide Chemical compound NC1=NC=C(C=C1C(=O)NC1CCCCC1)C1=CC=C(OCCCN2CCCCC2)C=C1 FJHJLNXCFAIWOY-UHFFFAOYSA-N 0.000 claims 1
- ZROZDTQXWWJRDP-UHFFFAOYSA-N 2-amino-N-cyclohexyl-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)NC1CCCCC1 ZROZDTQXWWJRDP-UHFFFAOYSA-N 0.000 claims 1
- QLKTYOQNNHTKLX-UHFFFAOYSA-N 2-amino-N-cyclohexyl-5-[4-(morpholine-4-carbonyl)phenyl]pyridine-3-carboxamide Chemical compound NC1=NC=C(C=C1C(=O)NC1CCCCC1)C1=CC=C(C=C1)C(=O)N1CCOCC1 QLKTYOQNNHTKLX-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 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
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- C—CHEMISTRY; METALLURGY
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
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- Orthopedic Medicine & Surgery (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662364620P | 2016-07-20 | 2016-07-20 |
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| FI3971177T3 true FI3971177T3 (fi) | 2024-07-30 |
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| CN115038443A (zh) | 2019-11-22 | 2022-09-09 | 因西特公司 | 包含alk2抑制剂和jak2抑制剂的组合疗法 |
| CN111170893B (zh) * | 2020-01-19 | 2022-04-26 | 郑州依米花手性药物研究有限公司 | Lefamulin的中间体化合物及其在Lefamulin制备中的应用 |
| WO2021257532A1 (en) * | 2020-06-16 | 2021-12-23 | Incyte Corporation | Alk2 inhibitors for the treatment of anemia |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
| CN116478145B (zh) * | 2022-04-13 | 2024-02-02 | 杭州邦顺制药有限公司 | Alk2激酶抑制剂 |
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| JP4901102B2 (ja) | 2002-05-03 | 2012-03-21 | エクセリクシス, インク. | プロテインキナーゼモジュレーターおよびその使用方法 |
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| 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 |
| CA2514733A1 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
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| BRPI0511571A (pt) | 2004-05-27 | 2008-01-02 | Pfizer | derivados de aminopiridina como agonistas de dopamina d3 seletivos |
| SA05260265A (ar) | 2004-08-30 | 2005-12-03 | استرازينيكا ايه بي | مركبات جديدة |
| RU2007141401A (ru) | 2005-04-08 | 2009-05-20 | ЭЙСАЙ Ар энд Ди МЕНЕДЖМЕНТ КО., ЛТД. (JP) | Терапевтический агент для лечения дискинезии |
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| GB0517175D0 (en) | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
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| 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) |
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