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US 10,208,016 B2Granted
1-sulfonyl piperidine derivatives as modulators of prokineticin receptors
AssigneeTakeda Pharmaceutical Company Limited
InventorMartin Teall
Life of this patent
Estimating the term…
Abstract
The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof in which m, n, W, X, Y, Z, R1, R2, R3, R4 and R5 are as defined in the specification, compositions containing them and their use in therapy.
Claims26
A compound of formula
- or a pharmaceutically acceptable salt thereof, wherein in formula (IA)
- W, X, Y and Z each independently represent N, NH or CH, with the proviso that W, X, Y and Z do not each simultaneously represent a moiety CH;
- m is 0, 1, 2 or 3;
- each R1 independently represents halogen, cyano, C1-C6 alkoxy, C3-C6 cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkyl, C1-C6 halo alkoxy, C1-C6 alkylthio, C1-C6 alkylcarbonyl, or C1-C6 alkyl optionally substituted by carboxyl or C1-C6 alkoxycarbonyl;
- n is 0, 1, 2, 3 or 4;
- each R2 independently represents halogen, cyano, carboxyl, hydroxyl, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 hydroxyalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyC1-C6 alkyl or a 5- to 9-membered heterocyclic ring system;
- R6 represents a hydrogen or halogen atom or a cyano, C1-C6 alkyl or C1-C6 alkoxycarbonyl group;
- R4 represents a 6- to 10-membered aromatic or heteroaromatic ring system, the ring system itself being optionally substituted by at least one substituent selected from halogen, hydroxyl, cyano, oxo, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulphinyl, C1-C6 alkylsulphonyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyl, amino, —CON(R9)2, C1-C6 alkylamino, di-(C1-C6 alkyl)amino, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy or C3-C6 cycloalkylmethyl;
- and
- each R9 independently represents a hydrogen atom or a C1-C6 alkyl group;
- provided that the compound of formula (IA) is not:
- 1-[(1-methyl-1H-pyrazol-4-yl)sulfonyl]-4-(phenylmethylene)piperidine;
- or
- 1-[(5-chloro-1-methyl-1H-imidazol-4-yl)sulfonyl]-4-[(3-fluorophenyl)methylene]piperidine.
11 more elements
A compound of formula
- or a pharmaceutically acceptable salt thereof, wherein in formula (IB)
- W, X, Y and Z each independently represent N, NH or CH, with the proviso that W, X, Y and Z do not each simultaneously represent a moiety CH;
- m is 1, 2 or 3;
- each R1 independently represents halogen, cyano, C1-C6 alkoxy, C3-C6 cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylcarbonyl, or C1-C6 alkyl optionally substituted by carboxyl or C1-C6 alkoxycarbonyl, with the proviso that there is at least one R1 group present that represents a C3-C6 cycloalkyl group;
- n is 0, 1, 2, 3 or 4;
- each R2 independently represents halogen, cyano, carboxyl, hydroxyl, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 hydroxyalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyC1-C6 alkyl or a 5- to 9-membered heterocyclic ring system;
- R5 represents a hydrogen atom or a substituent as defined above for R2;
- R7 and R8 each independently represent a hydrogen or halogen atom or cyano, carboxyl, hydroxyl, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 hydroxyalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyC1-C6 alkyl or a 5- to 9-membered heterocyclic ring system;
- R4 represents a 6- to 10-membered aromatic or heteroaromatic ring system, the ring system itself being optionally substituted by at least one substituent selected from halogen, hydroxyl, cyano, oxo, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulphinyl, C1-C6 alkylsulphonyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyl, amino, —CON(R9)2, C1-C6 alkylamino, di-(C1-C6 alkyl)amino, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy or C3-C6 cycloalkylmethyl;
- and
- each R9 independently represents a hydrogen atom or a C1-C6 alkyl group;
- provided that the compound of formula (IB) is not:
- 1-[[1-cyclopentyl-3-(1,1-dimethylethyl)-1H-pyrazol-4-yl]sulfonyl]-4-(phenylmethyl)piperidine;
- or
- 1-[(1-cyclopentyl-3-methyl-1H-pyrazol-4-yl)sulfonyl]-4-(phenylmethyl)piperidine.
12 more elements
Dependencies are inferred from the claim text.