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US 8,012,981 B2Granted
Benzylpiperazine derivatives as motilin receptor agonists
AssigneeGlaxo Group Limited
InventorsJonathan Thomas Seal, Geoffrey Stemp, Mervyn Thompson, Susan Marie Westaway
Life of this patent
Estimating the term…
Abstract
The invention relates to compounds of formula (I): processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of conditions or disorders which are mediated via the GPR38 receptor.
Claims22
A compound of formula (I):
- wherein:
- A is phenyl or pyridyl, optionally substituted with halogen, C(1-4)alkyl or C(1-4)alkoxy;
- R1 and R2 are independently H or C(1-4) alkyl;
- R3 is an optionally substituted phenyl, wherein when R3 is a substituted phenyl, said substituted phenyl has 1, 2 or 3 substituents, each independently selected from halogen, C(1-4)alkyl, C(1-4)alkoxy, C(3-7)cycloalkyl, hydroxy, trifluoromethoxy, trifluoromethyl, nitro, cyano, phenyl, NH2, NHR5, NR5R6, NHCOR5, NHSO2R5, C(O)CF3, C(O)C(1-4)alkyl, C(O)C(3-7)cycloalkyl, C(O)OC(1-4)alkyl, C(O)OC(3-7)cycloalkyl, OC(O)C(1-4)alkyl, OC(O)C(3-7)cycloalkyl, CONH2, CONHR5, CONR5R6, SOR6, SO2CF3, SO2R6, OSO2R6, OSO2CF3, SO2NH2, SO2NHR5 and SO2NR5R6;
- wherein R5 and R6 may be the same or different and are independently selected from C(1-4)alkyl, phenyl optionally substituted with halogen, and 5 or 6 membered heteroaryl optionally substituted with halogen;
- Y is NH, O, CH2 or a bond;
- and
- R4 is C(1-4) alkyl or C(1-4) alkoxy C(1-4) alkyl;
- or a salt thereof.
6 more elements
A compound selected from the group consisting of:
- 4-[(3-fluorophenyl)amino]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-[(4-fluorophenyl)amino]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-[(3-cyanophenyl)amino]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-[(2-fluorophenyl)amino]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-[(4-cyanophenyl)amino]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-{[2-(aminocarbonyl)phenyl]amino}-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-[(3-fluorophenyl)oxy]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-[(2-cyanophenyl)amino]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-{[3-fluoro-4-(methyloxy)phenyl]amino}-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-{[4-fluoro-3-(methyloxy)phenyl]amino}-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-[(3-fluorophenyl)amino]-N-methyl-N-(4-{[(3R)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- N-(4-{[(3R,5S)-3,5-dimethyl-1-piperazinyl]methyl}phenyl)-4-[(3-fluorophenyl)amino]-N-methyl-1-piperidinecarboxamide;
- 4-[(3-cyanophenyl)amino]-N-methyl-N-[4-(1-piperazinylmethyl)phenyl]-1-piperidinecarboxamide;
- 4-[(3-fluorophenyl)amino]-N-methyl-N-[4-(1-piperazinylmethyl)phenyl]-1-piperidinecarboxamide;
- 4-[(4-fluorophenyl)amino]-N-methyl-N-[4-(1-piperazinylmethyl)phenyl]-1-piperidinecarboxamide;
- 4-(4-fluorophenyl)-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-(3-fluorophenyl)-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-(3-cyanophenyl)-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-[(3 --fluorophenyl)amino]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- 4-[(3-fluorophenyl)amino]-N-methyl-N-(3-methyl-4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide;
- and
- 4-[(3-fluorophenyl)amino]-N-methyl-N-(6-{[(3S)-3-methyl-1-piperazinyl]methyl}-3-pyridinyl)-1-piperidinecarboxamide;
- or a pharmaceutically acceptable salt thereof.
20 more elements
A compound which is 4-[(3-fluorophenyl)amino]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide.
Dependencies are inferred from the claim text.