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US 11,440,884 B2Granted
Compounds, salts thereof and methods for treatment of diseases
AssigneeACADIA Pharmaceuticals Inc.
InventorsEthan S. Burstein, Roger Olsson, Karl Erik Jansson, Niklas Patrik Sköld, Larisa Yudina Wahlström, Björn Gustav Borgström, Henrik Von Wachenfeldt, Magnus Gustav Wilhelm Bergner
Life of this patent
Estimating the term…
Abstract
The present disclosure relates to compounds according to Formulae (I), (II) and (VIII), useful for treating diseases.
Claims17
A compound according to Formula (1)
- or a pharmaceutically acceptable salt;
- hydrate, solvate, stereoisomer, or deuterated analogue thereof, wherein:
- m and n are independently an integer selected from the group consisting of 0, 1, 2, and 3;
- p and q are independently an integer selected from the group consisting of 0, 1, 2, 3, and 4;
- R1 and R1d are fluoro;
- R1a, R1b, and R1c are hydrogen;
- R2, R2a, R2b, R2c and R2d are independently selected from the group consisting of hydrogen, deuterium;
- amino, hydroxyl, -OD, halogen, cyano, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C1-6 haloalkyl, unsubstituted or substituted C1-6 hydroxyalkyl, unsubstituted or substituted C2-6 alkenyl, unsubstituted or substituted C1-6 alkoxy, unsubstituted or substituted C3-6 cycloalkyl, unsubstituted or substituted C3-6 heteroalicyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, wherein at least one of R2, R2a, R2b, R2c and R2d is not hydrogen, or R2 and R2b or R2c, taken together with the atoms to which they are attached form a ring system;
- R3 is selected from the group consisting of hydrogen, deuterium, hydroxyl, -OD, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C1-6 haloalkyl, unsubstituted or substituted C1-6 hydroxyalkyl, unsubstituted or substituted C2-6 alkenyl, unsubstituted or substituted C3-6 cycloalkyl, unsubstituted or substituted C3-6 heteroalicyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
- or
- R3, the nitrogen to which R3 is attached and a carbon atom adjacent to the nitrogen taken together with R6 or R7 form a heteroalicyclic ring system;
- R4a, R4b, R5a, and R5b, are independently selected from the group consisting of hydrogen, deuterium, and unsubstituted or substituted C1-6 alkyl;
- R6 is selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, oxo, -OD, cyano, substituted or unsubstituted C1-4 alkyl, and substituted or unsubstituted C1-4 alkoxy, and substituted or unsubstituted aryl;
- R7 is selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, oxo, -OD, cyano, substituted or unsubstituted C1-4 alkyl, and substituted or unsubstituted C1-4 alkoxy;
- R8 is absent, or selected from the group consisting of hydrogen, deuterium, cyano, hydroxyl, -OD, substituted or unsubstituted C1-4 alkyl, substituted or unsubstituted C2-4 alkenyl, substituted or unsubstituted C3-6 cycloalkyl, and substituted or unsubstituted C1-4 alkoxy;
- A is —O—;
- and
- X is O or S.
15 more elements
A compound, pharmaceutically acceptable salt, polymorph, or stereoisomer selected from the group consisting of:
- [4-(propan-2-yloxy)phenyl]methyl N-[(2,4-difluorophenyl)methyl]-N-(piperidin-4-yl)carbamate;
- [4-(propan-2-yloxy)phenyl]methyl N-[(2,4-difluorophenyl)methyl]-N-(1-methylpiperidin-4-yl)carbamate;
- [4-(2-methylpropoxy)phenyl]methyl N-[(2,4-difluorophenyl)methyl]-N-(1-methylpiperidin-4-yl)carbamate;
- (4-methoxyphenyl)methyl N-[(2,4-difluorophenyl)methyl]-N-(1-methylpiperidin-4-yl)carbamate;
- N-[(2,4-difluorophenyl)methyl]-N-(1-methylpiperidin-4-yl){[(4-methoxyphenyl)methyl]sulfanyl}formamide;
- 4-(allyloxy)benzyl (2,4-difluorobenzyl)(1-methylpiperidin-4-yl)carbamate,
- 4-ethoxybenzyl (2,4-difluorobenzyl)(1-methylpiperidin-4-yl)carbamate;
- 4-(3-fluoropropoxy)benzyl (2,4-difluorobenzyl)(1-methylpiperidin-4-yl)carbamate;
- 4-((1,3-difluoropropan-2-yl)oxy)benzyl (2,4-difluorobenzyl)(1-methylpiperidin-4-yl)carbamate;
- 4-(2-hydroxy-2-methylpropoxy)benzyl (2,4-difluorobenzyl)(1-methylpiperidin-4-yl)carbamate;
- 4-cyclopropoxybenzyl (2,4-difluorobenzyl)(1-methylpiperidin-4-yl)carbamate;
- [4-(2-fluoroethoxy)phenyl]methyl N-[(2,4-difluorophenyl)methyl]-N-(1-methylpiperidin-4-yl)carbamate;
- (4-butoxyphenyl)methyl N-[(2,4-difluorophenyl)methyl]-N-(1-methylpiperidin-4-yl)carbamate;
- methyl 3-(4-}[(2,4-difluorophenyl)methyl](}[4-(propan-2-yloxy)phenyl]methoxy}carbonyl)amino}piperidin-1-yl)-2,2-dimethylpropanoate;
- 3-(4-{[(2,4-difluorophenyl)methyl]({[4-(propan-2-yloxy)phenyl]-methoxy}carbonyl)amino}piperidin-1-yl)-2,2-dimethylpropanoic acid;
- [4-(propan-2-yloxy)phenyl]methyl N-[(2,4-difluorophenyl)methyl]-N-(1-ethylpiperidin-4-yl)carbamate;
- [4-(propan-2-yloxy)phenyl]methyl N-(1-cyclopropylpiperidin-4-yl)-N-[(2,4-difluorophenyl)methyl]carbamate;
- [4-(propan-2-yloxy)phenyl]methyl N-[(2,4-difluorophenyl)methyl]-N-[1-(oxetan-3-yl)piperidin-4-yl]carbamate;
- (2E)-N-[(2,4-difluorophenyl)methyl]-N-(1-methylpiperidin-4-yl)-3-[4-(propan-2-yloxy)phenyl]prop-2-enamide;
- N-[(2,4-dichlorophenyl)methyl]-N-(1-methylpiperidin-4-yl)-2[4-(2-methylpropoxy)phenyl]acetamide;
- N-[(2,4-dichlorophenyl)methyl]-N-(1-methylpiperidin-4-yl)-2-[4-(propan-2-yloxy)phenyl]acetamide;
- 4-(tert-butoxy)benzyl (2,4-difluorobenzyl)(1-methylpiperidin-4-yl)carbamate;
- and
- 4-(1,1-difluoroethyl)benzyl (2,4-difluorobenzyl)(1-methylpiperidin-4-yl)carbamate.
21 more elements
Dependencies are inferred from the claim text.