Novel compounds
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Abstract
A compound of Formula (I)
and pharmaceutically and/or veterinarily acceptable derivatives thereof, wherein R1 is H, C1-6alkyl, —C(X)Y, C3-8cycloalkyl, aryl, het, aryl-C1-4alkyl or het-C1-4alkyl, wherein the cycloalkyl, aryl or het groups are optionally substituted by at least one substituent independently selected from C1-8alkyl, C1-8alkoxy, OH, halo, CF3, OCF3, SCF3, hydroxy-C1-6alkyl, C1-4alkoxy-C1-6alkyl and C1-4alkyl-S—C1-4alkyl; R2 is aryl or heteroaryl, each optionally substituted by at least one substituent independently selected from C1-8alkyl, C1-8alkoxy, OH, halo, CF3, OCF3, SCF3, hydroxy-C1-6alkyl, C1-4alkoxy-C1-6alkyl and C1-4alkyl-S—C1-4alkyl; R3 is C1-6alkyl, C3-8cycloalkyl, C3-8cycloalkyl-C1-6alkyl, aryl, het, aryl-C1-4alkyl or het-C1-4alkyl, wherein the cycloalkyl, aryl or het groups are optionally substituted by at least one substituent independently selected from C1-6alkyl, C1-6alkoxy, OH, halo, CF3, OCF3, SCF3, hydroxy-C1-6alkyl, C1-4alkoxy —C1-6alkyl and C1-4alkyl-S—C1-4alkyl; X is S or O; Y is H, C1-6alkyl, aryl, het, aryl-C1-4alkyl or het-C1-4alkyl; and n is 1 or 2, provided that when n is 1, m is 0 or 1 and when n is 2, m is 0, wherein if m is 0, then * represents a chiral center. The compounds of the invention exhibit activity as both serotonin and noradrenaline re-uptake inhibitors and therefore have utility in a variety of therapeutic areas, for example urinary incontinence.
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Citations
18 Claims
- 1. A compound of Formula (I)
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10. The compound:
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2,3-dichloro-N-isobutyl-N-[(3S)-pyrrolidin-3-yl]benzamide;
2,4-dichloro-N-isobutyl-N-[(3S)-pyrrolidin-3-yl]benzamide;
2-chloro-3-methyl-N-isobutyl-N-[(3S)-pyrrolidin-3-yl]benzamide;
3-fluoro-2-methyl-N-isobutyl-N-[(3S)-pyrrolidin-3-yl]benzamide;
3-methoxy-2-methyl-N-isobutyl-N-[(3S)-pyrrolidin-3-yl]benzamide;
3-chloro-N-isobutyl-N-[(3S)-pyrrolidin-3-yl]benzamide;
4-chloro-N-isobutyl-N-[(3S)-pyrrolidin-3-yl]benzamide;
3,4-dichloro-N-isobutyl-N-[(3S)-pyrrolidin-3-yl]benzamide;
N-(2-naphthylmethyl)-N-[(3S)-pyrrolidin-3-yl]benzamide;
N-(2-naphthylmethyl)-N-[(3R)-pyrrolidin-3-yl]benzamide;
N-isobutyl-N-[(3S)-pyrrolidin-3-yl]-2-naphthamide;
N-butyl-N-[(3S)-pyrrolidin-3-yl]-1-naphthamide;
4-chloro-N-(3,4-dichlorobenzyl)-N-[(3R)-pyrrolidin-3-yl]benzamide;
N-pyrrolidin-3-yl-N-(5, 6,7,8-tetrahydro-naphthalen-1-ylmethyl)-benzamide;
N-(2,4-dichloro-benzyl)-N-pyrrolidin-3-yl-benzamide;
N-(3-chloro-4-methyl-benzyl)-2-fluoro-N-pyrrolidin-3-yl-benzamide;
naphthalene-2-carboxylic acid butyl-pyrrolidin-3-yl-amide;
naphthalene-2-carboxylic acid isobutyl-pyrrolidin-3-yl-amide;
naphthalene-2-carboxylic acid (2,2-dimethyl-propyl)-pyrrolidin-3-yl-amide;
3-chloro-N-isobutyl-4-methyl-N-pyrrolidin-3-yl-benzamide;
N-isobutyl-2,3-dimethyl-N-pyrrolidin-3-yl-benzamide;
3-chloro-N-(2,2-dimethyl-propyl)-2-methyl-N-pyrrolidin-3-yl-benzamide;
2-chloro-4-fluoro-N-isobutyl-N-pyrrolidin-3-yl-benzamide;
2-chloro-N-isobutyl-N-pyrrolidin-3-yl-benzamide;
3-chloro-2-fluoro-N-isobutyl-N-pyrrolidin-3-yl-benzamide;
3-chloro-4-fluoro-N-isobutyl-N-pyrrolidin-3-yl-benzamide;
N-butyl-2,4-dichloro-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-cyclobutylmethyl-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-cyclopentylmethyl-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-(2,2-dimethyl-propyl)-2-methyl-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-(2-ethyl-butyl)-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-(3-methyl-butyl)-N-pyrrolidin-3-yl-benzamide;
2,3,4-trichloro-N-isobutyl-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-(2-cyclopropyl-ethyl)-N-pyrrolidin-3-yl-benzamide;
naphthalene-1-carboxylic acid isobutyl-pyrrolidin-3-yl-amide;
2,4-dichloro-5-fluoro-N-isobutyl-N-pyrrolidin-3-yl-benzamide;
2,3-dichloro-N-(2,2-dimethyl-propyl)-N-pyrrolidin-3-yl-benzamide;
2,3-dichloro-N-(3-methyl-butyl)-N-pyrrolidin-3-yl-benzamide;
2,3-dichloro-N-cyclobutylmethyl-N-pyrrolidin-3-yl-benzamide;
2,3-dichloro-N-cyclopentyl-N-pyrrolidin-3-yl-benzamide;
3,4-dichloro-N-cyclopentyl-N-pyrrolidin-3-yl-benzamide;
2,3-dichloro-N-(1,2-dimethyl-propyl)-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-(1,2-dimethyl-propyl)-N-pyrrolidin-3-yl-benzamide;
2,3-dichloro-N-cyclohexyl-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-cyclopentyl-N-pyrrolidin-3-yl-benzamide;
3,4-dichloro-N-cyclopentyl-N-pyrrolidin-3-yl-benzamide;
naphthalene-1-carboxylic acid sec-butyl-pyrrolidin-3-yl-amide;
N-sec-butyl-2,3-dichloro-N-pyrrolidin-3-yl-benzamide;
N-sec-butyl-2,4-dichloro-N-pyrrolidin-3-yl-benzamide;
2,3-dichloro-N-(1-ethyl-propyl)-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-(1-ethyl-propyl)-N-pyrrolidin-3-yl-benzamide;
naphthalene-1-carboxylic acid (1-ethyl-propyl)-pyrrolidin-3-yl-amide;
2,3-dichloro-N-cyclobutyl-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-cyclobutyl-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-cyclopentyl-N-pyrrolidin-3-yl-benzamide;
2,3-dichloro-N-pyrrolidin-3-yl-N-(1,2,2-trimethyl-propyl)-benzamide;
N-tert-butyl-2,3-dichloro-N-pyrrolidin-3-yl-benzamide;
naphthalene-1-carboxylic acid cyclopentyl-pyrrolidin-3-yl-amide;
2,3-dichloro-N-phenyl-N-pyrrolidin-3-yl-benzamide;
3,4-dichloro-N-(2,2-dimethyl-propyl)-2-methyl-N-pyrrolidin-3-yl-benzamide;
3-chloro-N-isobutyl-2-methyl-N-pyrrolidin-3-yl-benzamide;
N-butyl-2,3-dichloro-N-pyrrolidin-3-yl-benzamide;
N-butyl-3,4-dichloro-N-pyrrolidin-3-yl-benzamide;
naphthalene-2-carboxylic acid cyclobutylmethyl-pyrrolidin-3-yl-amide;
naphthalene-1-carboxylic acid cyclobutylmethyl-pyrrolidin-3-yl-amide;
3,4-dichloro-N-cyclobutylmethyl-N-pyrrolidin-3-yl-benzamide;
4-chloro-N-isobutyl-2-methoxy-N-pyrrolidin-3-yl-benzamide;
4-chloro-N-isobutyl-3-methyl-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-isobutyl-3-methyl-N-pyrrolidin-3-yl-benzamide;
naphthalene-1-carboxylic acid (3-methyl-butyl)-pyrrolidin-3-yl-amide;
naphthalene-1-carboxylic acid (2,2-dimethyl-propyl)-pyrrolidin-3-yl-amide;
3,4-dichloro-N-(3-methyl-butyl)-N-pyrrolidin-3-yl-benzamide;
2,3-dichloro-N-(4-fluoro-phenyl)-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-N-(4-fluoro-phenyl)-N-pyrrolidin-3-yl-benzamide;
naphthalene-1-carboxylic acid (4-fluoro-phenyl)-pyrrolidin-3-yl-amide;
N-butyl-2,3,4-trichloro-N-pyrrolidin-3-yl-benzamide;
2,3,4-trichloro-N-cyclobutylmethyl-N-pyrrolidin-3-yl-benzamide;
N-pyrrolidin-3-yl-N-(3-trifluoromethyl-benzyl)-benzamide;
2,4-dichloro-N-phenyl-N-pyrrolidin-3-yl-benzamide;
3,4-dichloro-N-phenyl-N-pyrrolidin-3-yl-benzamide;
2,3,4-trichloro-N-(2,2-dimethyl-propyl)-N-pyrrolidin-3-yl-benzamide;
naphthalene-1-carboxylic acid phenyl-pyrrolidin-3-yl-amide;
2,3,4-trichloro-N-(2-cyclopropyl-ethyl)-N-pyrrolidin-3-yl-benzamide;
2,3-dichloro-N-(2-cyclopropyl-ethyl)-N-pyrrolidin-3-yl-benzamide;
2-bromo-4-chloro-N-isobutyl-N-pyrrolidin-3-yl-benzamide;
4-chloro-2-ethoxy-N-isobutyl-N-pyrrolidin-3-yl-benzamide;
3-bromo-4-chloro-N-isobutyl-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-5-fluoro-N-isobutyl-N-[(3S)-pyrrolidin-3-yl]benzamide;
3,4-dichloro-N-isobutyl-2-methyl-N-pyrrolidin-3-yl-benzamide;
2,4-dichloro-3-fluoro-N-isobutyl-N-[pyrrolidin-3-yl]benzamide;
2,3-dichloro-4-fluoro-N-isobutyl-N-[pyrrolidin-3-yl]benzamide;
2,3-dichloro-5-fluoro-N-isobutyl-N-[pyrrolidin-3-yl]benzamide;
2,4,5-trichloro-N-isobutyl-N-[pyrrolidin-3-yl] benzamide;
2,5-dichloro-N-isobutyl-N-[pyrrolidin-3-yl]benzamide;
2,5-dichloro-4-fluoro-N-isobutyl-N-[pyrrolidin-3-yl]benzamide;
2,3,5-trichloro-N-isobutyl-N-[pyrrolidin-3-yl]benzamide;
2,3-dichloro-6-fluoro-N-isobutyl-N-[pyrrolidin-3-yl]benzamide;
3,4-dichloro-6-fluoro-N-isobutyl-N-[pyrrolidin-3-yl]benzamide;
3,4-dichloro-2-fluoro-N-isobutyl-N-[pyrrolidin-3-yl]benzamide;
2-chloro-3,6-difluoro-N-isobutyl-N-[pyrrolidin-3-yl]benzamide; and
4-chloro-N-(2,3-dichlorobenzyl)-N-[(3R)-pyrrolidin-3-yl]benzamide, or pharmaceutically and/or veterinarily acceptable derivatives thereof.
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11. The compound 2,3-dichloro-N-isobutyl-N-[(3S)-pyrrolidin-3-yl]benzamide, or pharmaceutically and/or veterinarily acceptable derivatives thereof.
Specification