Melanocortin type 4 receptor agonist piperidinoylpyrrolidines
AssigneePfizer Inc.
InventorsMark David Andrews, Alan Daniel Brown, Mark Ian Lansdell, Nicholas William Summerhill
Life of this patent
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Abstract
The present invention relates to a class of melanocortin MCR4 agonists of general formula (I) wherein the variables and substituents are as defined herein and especially to selective MCR4 agonist compounds, to their use in medicine, particularly in the treatment of sexual dysfunction and obesity, to intermediates useful in their synthesis and to compositions containing them.
Claims19
A compound of formula (I):
- wherein
- one of X and Y is N and the other is CH,
- R is F, Cl, CN, CF3 or methoxy, with the proviso that when Y is N, R is not F or Cl,
- R1 is phenyl, 2-pyridyl, C3-C6 cycloalkyl or CH2(C3-C6 cycloalkyl), wherein the ring moiety of said phenyl, 2-pyridyl, C3-C6 cycloalkyl or CH2(C3-C6 cycloalkyl) is optionally substituted with one to four substituents independently selected from F, Cl, CN, methyl and methoxy,
- R2 is H, F or Cl, with the proviso that when Y is N, R2 is not F or Cl,
- Het is a 6-membered ring containing one or 2 N atoms, wherein the ring is either aromatic, or contains 2 double bonds in the ring and a 0 substituent, which ring is optionally substituted with one to four substituents independently selected from F, Cl, OH, CN, methyl, ethyl, NH2, NHCH3, N(CH3)2 and methoxy,
- or alternatively, Het is a 6-membered ring containing one or 2 N atoms fused at the 3,4-positions, relative to the attachment to the pyrrolidine ring, to a 5-membered aromatic ring containing one or two further N atoms, which 5-membered ring is optionally substituted with OH,
- or a pharmaceutically acceptable salt thereof.
The compound 6-[(3S,4S)-3-{[(3R,4R,5S)-4-(4-chlorophenyl)-4-hydroxy-3,5-dimethylpiperidin-1-yl]carbonyl}-4-(5-chloropyridin-2-yl)pyrrolidin-1-yl]-2-methylpyridazin-3(2H)-one or a pharmaceutically acceptable salt thereof.
A pharmaceutical composition comprising a therapeutically effective amount of 6-[(3S,4S)-3-{[(3R,4R,5S)-4-(4-chlorophenyl)-4-hydroxy-3,5-dimethylpiperidin-1-yl]carbonyl}-4-(5-chloropyridin-2-yl)pyrrolidin-1-yl]-2-methylpyridazin-3(2H)-one or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable diluent, carrier or adjuvant.
Dependencies are inferred from the claim text.