CA2530159A1 - N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenaline re-uptake inhibitors - Google Patents
N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenaline re-uptake inhibitors Download PDFInfo
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- CA2530159A1 CA2530159A1 CA002530159A CA2530159A CA2530159A1 CA 2530159 A1 CA2530159 A1 CA 2530159A1 CA 002530159 A CA002530159 A CA 002530159A CA 2530159 A CA2530159 A CA 2530159A CA 2530159 A1 CA2530159 A1 CA 2530159A1
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- pyrrolidin
- benzamide
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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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-Cl_4alkyl or het-Cl_4alkyl, wherein the cycloalkyl, aryl or het groups are optionally substituted by at least one substituent independently selected from C1_8allkyl, C1_8alkoxy, OH, halo, CF3, OCF3, SCF3, hydroxy-Cl_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-Cl_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.
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.
Claims (24)
1. 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 C1-8allkyl, C1-8alkoxy, OH, halo, CF3, OCF3, SCF3, hydroxy-C1-8alkyl, C1-4alkoxy-C1-8alkyl 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;
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 centre;
aryl is phenyl, naphthyl, anthracyl or phenanthryl;
heteroaryl is an aromatic 5- or 6- membered heterocycle which contains at least one N, O or S heteroatom, optionally fused to an aryl group;
het is an aromatic or non-aromatic 4-, 5- or 6- membered heterocycle which contains at least one N, O or S heteroatom, optionally fused to a 5-or 6- membered carbocyclic group or a second 4-, 5- or 6-membered heterocycle which contains at least one N, O or S heteroatom.
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;
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 centre;
aryl is phenyl, naphthyl, anthracyl or phenanthryl;
heteroaryl is an aromatic 5- or 6- membered heterocycle which contains at least one N, O or S heteroatom, optionally fused to an aryl group;
het is an aromatic or non-aromatic 4-, 5- or 6- membered heterocycle which contains at least one N, O or S heteroatom, optionally fused to a 5-or 6- membered carbocyclic group or a second 4-, 5- or 6-membered heterocycle which contains at least one N, O or S heteroatom.
2. A compound according to Claim 1, wherein R1 is H.
3. A compound according to Claim 1 or Claim 2, wherein m is 0 and represents the R or S enantiomer.
4. A compound according to Claim 3, wherein * represents the S
enantiomer.
enantiomer.
5. A compound according to any preceding claim, wherein R2 is phenyl, naphthyl or quinolinyl, 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.
6. A compound according to Claim 5, wherein R2 is phenyl or naphthyl each optionally substituted by one, two or three substituents independently selected from halo, OH, C1-4alkyl and CF3.
7. A compound according to any preceding claim, wherein R3 is C1-6alkyl, C3-8cycloalkyl, C3-8cycloalkyl-C1-4alkyl or aryl-C1-4alkyl.
8. A compound according to Claim 7, wherein R3 is C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-2alkyl, phenyl-CH2- or naphthyl-Ch2-.
9. A compound according to Claim 1, wherein R1 is H;
R2 is phenyl or naphthyl each optionally substituted by one, two or three substituents independently selected from halo, OH, C1-4alkyl and CF3;
R3 is C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-3alkyl, phenyl-CH2- or naphthyl-CH2-; and m is 0.
R2 is phenyl or naphthyl each optionally substituted by one, two or three substituents independently selected from halo, OH, C1-4alkyl and CF3;
R3 is C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-3alkyl, phenyl-CH2- or naphthyl-CH2-; and m is 0.
10. A compound according to Claim 1, selected from:
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.
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.
11. A compound according to Claim 10 which is 2,3-Dichloro-N-isobutyl-N-[(3S)-pyrrolidin-3-yl]benzamide or pharmaceutically and/or veterinarily acceptable derivatives thereof.
12. A pharmaceutical composition comprising a compound as claimed in any one of Claims 1 to 11 and a pharmaceutically acceptable adjuvant, diluent or carrier.
13. A compound according to any one of Claims 1-11 for use as a medicament.
14. Use of a compound according to any one of Claims 1-11 in the manufacture of a medicament for the treatment of a disorder in which the regulation of monoamine transporter function in mammals is implicated.
15. Use of a compound according to any one of Claims 1-11 in the manufacture of a medicament for the treatment of a disorder in which the regulation of serotonin or noradrenaline in mammals is implicated.
16. Use according to Claim 15, wherein the regulation of serotonin and noradrenaline is implicated.
17. Use of a compound according to any one of Claims 1-11 in the manufacture of a medicament for the treatment of urinary disorders, depression, pain, premature ejaculation, ADHD or fibromyalgia in mammals.
18. Use of a compound according to Claim 17, for the treatment of urinary incontinence, such as GSI or USI, in mammals.
19. A method of treatment of a disorder in which the regulation of monoamine transporter function is implicated which comprises administering a therapeutically effective amount of a compound according to any one of Claims 1-11 to a patient in need of such treatment.
20. A method of treatment of a disorder in which the regulation of serotonin or noradrenaline is implicated which comprises administering a therapeutically effective amount of a compound according to any one of Claims 1-11 to a patient in need of such treatment.
21. A method according to Claim 20, wherein the regulation of serotonin and noradrenaline is implicated.
22. A method of treatment of urinary disorders, depression, pain, premature ejaculation, ADHD or fibromyalgia, which comprises administering a therapeutically effective amount of a compound according to any one of Claims 1-11 to a patient in need of such treatment.
23. A method according to Claim 22, wherein the urinary disorder is urinary incontinence, such as GSI or USI.
24. A process for preparing a compound according to any one of Claims 1-11 comprising reacting a compound of formula (X):
wherein R3, n and m are as defined above and Y is R1 or a protecting group, with an acid or acyl halide: R2COX, wherein X is OH or halo, and deprotecting if necessary or desired.
wherein R3, n and m are as defined above and Y is R1 or a protecting group, with an acid or acyl halide: R2COX, wherein X is OH or halo, and deprotecting if necessary or desired.
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GBGB0314048.0A GB0314048D0 (en) | 2003-06-17 | 2003-06-17 | Novel compounds |
US49312603P | 2003-08-06 | 2003-08-06 | |
US60/493,126 | 2003-08-06 | ||
PCT/IB2004/001943 WO2004110995A1 (en) | 2003-06-17 | 2004-06-07 | N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenaline re-uptake inhibitors |
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CA2530159C CA2530159C (en) | 2010-02-02 |
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CA (1) | CA2530159C (en) |
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- 2005-11-21 IS IS8136A patent/IS8136A/en unknown
- 2005-12-14 HR HR20050993A patent/HRP20050993A2/en not_active Application Discontinuation
- 2005-12-16 EC EC2005006232A patent/ECSP056232A/en unknown
- 2005-12-16 MA MA28674A patent/MA27885A1/en unknown
-
2008
- 2008-05-21 US US12/124,755 patent/US20080306123A1/en not_active Abandoned
- 2008-07-09 HR HR20080339T patent/HRP20080339T3/en unknown
- 2008-08-14 CY CY20081100869T patent/CY1110434T1/en unknown
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