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
- Publication number
- 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
- Authority
- CA
- Canada
- Prior art keywords
- pyrrolidin
- benzamide
- dichloro
- isobutyl
- 4alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0314048.0A GB0314048D0 (en) | 2003-06-17 | 2003-06-17 | Novel compounds |
GBGB0314048.0 | 2003-06-17 | ||
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 |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2530159A1 true CA2530159A1 (en) | 2004-12-23 |
CA2530159C CA2530159C (en) | 2010-02-02 |
Family
ID=33554153
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002530159A Expired - Fee Related CA2530159C (en) | 2003-06-17 | 2004-06-07 | N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenaline re-uptake inhibitors |
Country Status (31)
Country | Link |
---|---|
US (2) | US7378436B2 (en) |
EP (1) | EP1638933B1 (en) |
JP (1) | JP4137159B2 (en) |
KR (1) | KR100803796B1 (en) |
AP (1) | AP2005003467A0 (en) |
AR (1) | AR044715A1 (en) |
AT (1) | ATE398107T1 (en) |
AU (1) | AU2004247487B2 (en) |
BR (1) | BRPI0411594A (en) |
CA (1) | CA2530159C (en) |
CY (1) | CY1110434T1 (en) |
DE (1) | DE602004014372D1 (en) |
DK (1) | DK1638933T3 (en) |
EA (1) | EA009881B1 (en) |
EC (1) | ECSP056232A (en) |
ES (1) | ES2305776T3 (en) |
HR (2) | HRP20050993A2 (en) |
IL (1) | IL172063A0 (en) |
IS (1) | IS8136A (en) |
MA (1) | MA27885A1 (en) |
MX (1) | MXPA05013960A (en) |
NL (1) | NL1026438C2 (en) |
NZ (1) | NZ544046A (en) |
PA (1) | PA8605301A1 (en) |
PE (1) | PE20050631A1 (en) |
PL (1) | PL1638933T3 (en) |
PT (1) | PT1638933E (en) |
SI (1) | SI1638933T1 (en) |
TW (1) | TW200505852A (en) |
UY (1) | UY28360A1 (en) |
WO (1) | WO2004110995A1 (en) |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2417727C (en) | 2000-07-31 | 2009-09-01 | Nycomed Danmark A/S | Fentanyl composition for nasal administration |
NZ544046A (en) * | 2003-06-17 | 2009-08-28 | Pfizer | N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenaline re-uptake inhibitors |
JP5188807B2 (en) | 2004-10-18 | 2013-04-24 | イーライ リリー アンド カンパニー | 1- (Hetero) aryl-3-amino-pyrrolidine derivatives for use as mGluR3 receptor antagonists |
GB0425766D0 (en) * | 2004-11-23 | 2004-12-22 | Pfizer Ltd | Novel compounds |
US7122683B2 (en) | 2004-11-23 | 2006-10-17 | Pfizer Inc. | Amides useful as monoamine re-uptake inhibitors |
EP1828119A1 (en) * | 2004-12-14 | 2007-09-05 | Pfizer Limited | N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenalin re-uptake inhibitors |
CA2590229A1 (en) * | 2004-12-14 | 2006-06-22 | Pfizer Limited | N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenalin re-uptake inhibitors |
TWI439452B (en) | 2005-05-13 | 2014-06-01 | Otsuka Pharma Co Ltd | Pyrrolidine compound |
AU2006254256B2 (en) | 2005-06-02 | 2012-04-12 | F. Hoffmann-La Roche Ag | Piperidin-4-yl-amide derivatives and their use as SST receptor subtype 5 antagonists |
WO2007135530A2 (en) * | 2006-05-22 | 2007-11-29 | Pfizer Limited | Pharmaceutically & veterinarily suitable salt |
US20080014152A1 (en) * | 2006-07-13 | 2008-01-17 | Di Mauro Thomas M | Intranasal delivery of clenbuterol across the cribriform plate and into the brain |
JP5219465B2 (en) * | 2006-11-10 | 2013-06-26 | 大塚製薬株式会社 | Medicine |
JPWO2008093737A1 (en) * | 2007-01-31 | 2010-05-20 | 大日本住友製薬株式会社 | Amide derivatives |
JP2010189275A (en) * | 2007-06-14 | 2010-09-02 | Dainippon Sumitomo Pharma Co Ltd | Naphthalene derivative |
US8263652B2 (en) * | 2007-10-31 | 2012-09-11 | Sk Biopharmaceuticals Co., Ltd. | Stabilized pediatric suspension of carisbamate |
RU2010129690A (en) | 2007-12-19 | 2012-01-27 | Дайниппон Сумитомо Фарма Ко., Лтд. (Jp) | BICYCLIC HETEROCYCLIC DERIVATIVES |
EP2318362B1 (en) | 2008-07-24 | 2013-09-25 | Theravance, Inc. | 3-(phenoxyphenylmethyl)pyrrolidine compounds |
RU2503662C2 (en) | 2008-11-14 | 2014-01-10 | Тереванс, Инк. | Crystalline form of 4-[2-(2-fluorophenoxymethyl)phenyl]piperidine compound |
US20100267743A1 (en) * | 2009-04-15 | 2010-10-21 | Stangeland Eric L | 3-(phenoxypyrrolidin-3-yl-methyl)heteroaryl, 3-(phenylpyrrolidin-3-ylmethoxy)heteroaryl, and 3-(heteroarylpyrrolidin-3-ylmethoxy)heteroaryl compounds |
AU2010263641A1 (en) | 2009-06-24 | 2012-01-19 | Sumitomo Dainippon Pharma Co., Ltd. | N-substituted-cyclic amino derivative |
RU2535669C2 (en) | 2009-07-13 | 2014-12-20 | Тереванс, Инк. | 3-phenoxymethyl-pyrrolidine compounds |
US8273786B2 (en) | 2009-07-21 | 2012-09-25 | Theravance, Inc. | 3-phenoxymethylpyrrolidine compounds |
US8778949B2 (en) * | 2010-01-11 | 2014-07-15 | Theravance Biopharma R&D Ip, Llc | 1-(2-phenoxymethylphenyl)piperazine compounds |
WO2011119461A1 (en) * | 2010-03-22 | 2011-09-29 | Theravance, Inc. | 1-(2-phenoxymethylheteroaryl)piperidine and piperazine compounds |
CN103153950B (en) | 2010-10-11 | 2015-11-25 | 施万生物制药研发Ip有限责任公司 | serotonin reuptake inhibitors |
WO2012075239A1 (en) | 2010-12-03 | 2012-06-07 | Theravance, Inc. | Serotonin reuptake inhibitors |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE138773C (en) | ||||
US3963745A (en) * | 1972-04-03 | 1976-06-15 | A. H. Robins Company, Incorporated | Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides |
US4002757A (en) * | 1974-12-26 | 1977-01-11 | A. H. Robins Company, Incorporated | N-(1-substituted-3-pyrrolidinyl)-4-quinolinecarboxamides |
US4020072A (en) * | 1976-05-04 | 1977-04-26 | E. R. Squibb & Sons, Inc. | 5-Aminomethyl-1H-pyrazolo[3,4-b]pyridines |
GB1574419A (en) * | 1977-11-11 | 1980-09-03 | Anphar Sa | Piperidine compounds |
CH628885A5 (en) * | 1978-01-01 | 1982-03-31 | Anphar Sa | Piperidine derivative |
US5130312A (en) * | 1987-07-17 | 1992-07-14 | Janssen Pharmaceutica N.V. | Substituted N-(3-hydroxy-4-piperidinyl)benzamides |
FR2642069B1 (en) * | 1989-01-20 | 1991-04-12 | Rhone Poulenc Sante | NOVEL BENZOPYRAN DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
JP2000500502A (en) | 1995-11-22 | 2000-01-18 | メルク エンド カンパニー インコーポレーテッド | Farnesyl-protein transferase inhibitor |
WO1999065881A1 (en) | 1998-06-19 | 1999-12-23 | Nissan Chemical Industries, Ltd. | Heterocyclic compounds as hypoglycemic agents |
US6670299B1 (en) * | 1999-07-03 | 2003-12-30 | Northwestern University | Cyclopentadienyl-containing low-valent early transition metal olefin polymerization catalysts |
FR2802206B1 (en) * | 1999-12-14 | 2005-04-22 | Sod Conseils Rech Applic | 4-AMINOPIPERIDINE DERIVATIVES AND THEIR USE AS MEDICINAL PRODUCTS |
DK1311272T3 (en) | 2000-03-03 | 2007-02-26 | Eisai R&D Man Co Ltd | New methods using cholinesterase inhibitors |
DE60125335T2 (en) * | 2000-03-06 | 2007-07-12 | Acadia Pharmaceuticals Inc., San Diego | AZACYCLIC COMPOUNDS FOR USE IN THE TREATMENT OF SEROTONIN-RELATED DISEASES |
JP2004509891A (en) | 2000-09-22 | 2004-04-02 | スミスクライン ビーチャム パブリック リミテッド カンパニー | Pyrazolopyridine and pyrazolopyridazine as antidiabetic drugs |
JP2004509866A (en) | 2000-09-25 | 2004-04-02 | アクテリオン ファマシューティカルズ リミテッド | Substituted amino-aza-cycloalkanes |
WO2003024928A2 (en) | 2001-09-14 | 2003-03-27 | Novo Nordisk A/S | Novel aminoazetidine, -pyrrolidine and -piperidine derivatives |
WO2003037865A1 (en) | 2001-10-31 | 2003-05-08 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Novel anticancer compounds |
GB0128287D0 (en) | 2001-11-26 | 2002-01-16 | Smithkline Beecham Plc | Novel method and compounds |
IL165907A0 (en) * | 2002-06-24 | 2006-01-15 | Acadia Pharm Inc | N-substituted piperidine derivatives as serotonin receptor agents |
AU2003249983A1 (en) | 2002-07-18 | 2004-02-09 | Actelion Pharmaceuticals Ltd | Piperidines useful for the treatment of central nervous system disorders |
AU2003263393A1 (en) | 2002-09-04 | 2004-03-29 | Glenmark Pharmaceuticals Limited | New heterocyclic amide compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them |
CA2511242C (en) | 2002-12-20 | 2010-01-12 | Anita Melikian | Inhibitors of human tumor-expressed ccxckr2 |
NZ544046A (en) * | 2003-06-17 | 2009-08-28 | Pfizer | N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenaline re-uptake inhibitors |
-
2004
- 2004-06-07 NZ NZ544046A patent/NZ544046A/en unknown
- 2004-06-07 MX MXPA05013960A patent/MXPA05013960A/en active IP Right Grant
- 2004-06-07 AT AT04736241T patent/ATE398107T1/en not_active IP Right Cessation
- 2004-06-07 AP AP2005003467A patent/AP2005003467A0/en unknown
- 2004-06-07 DK DK04736241T patent/DK1638933T3/en active
- 2004-06-07 BR BRPI0411594-5A patent/BRPI0411594A/en not_active IP Right Cessation
- 2004-06-07 DE DE602004014372T patent/DE602004014372D1/en active Active
- 2004-06-07 EP EP04736241A patent/EP1638933B1/en active Active
- 2004-06-07 CA CA002530159A patent/CA2530159C/en not_active Expired - Fee Related
- 2004-06-07 PL PL04736241T patent/PL1638933T3/en unknown
- 2004-06-07 JP JP2006516540A patent/JP4137159B2/en not_active Expired - Fee Related
- 2004-06-07 WO PCT/IB2004/001943 patent/WO2004110995A1/en active IP Right Grant
- 2004-06-07 PT PT04736241T patent/PT1638933E/en unknown
- 2004-06-07 ES ES04736241T patent/ES2305776T3/en active Active
- 2004-06-07 EA EA200501730A patent/EA009881B1/en not_active IP Right Cessation
- 2004-06-07 AU AU2004247487A patent/AU2004247487B2/en not_active Expired - Fee Related
- 2004-06-07 SI SI200430767T patent/SI1638933T1/en unknown
- 2004-06-07 KR KR1020057024147A patent/KR100803796B1/en not_active IP Right Cessation
- 2004-06-14 PE PE2004000590A patent/PE20050631A1/en not_active Application Discontinuation
- 2004-06-14 UY UY28360A patent/UY28360A1/en not_active Application Discontinuation
- 2004-06-16 AR ARP040102082A patent/AR044715A1/en not_active Application Discontinuation
- 2004-06-16 TW TW093117317A patent/TW200505852A/en unknown
- 2004-06-16 PA PA20048605301A patent/PA8605301A1/en unknown
- 2004-06-17 NL NL1026438A patent/NL1026438C2/en not_active IP Right Cessation
- 2004-06-17 US US10/872,160 patent/US7378436B2/en not_active Expired - Fee Related
-
2005
- 2005-11-20 IL IL172063A patent/IL172063A0/en unknown
- 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
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2530159A1 (en) | N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenaline re-uptake inhibitors | |
FR2809396B1 (en) | NOVEL MOLECULES HAVING CALCIMIMETIC ACTIVITY AND THEIR METHOD OF PREPARATION | |
BR0315047A (en) | Compound, pharmaceutical composition comprising the same, process for preparing the pharmaceutical composition, use of the compounds, method of treatment and process for the preparation of the compound | |
DK496089D0 (en) | BIOLOGICALLY ACTIVE PHENYLALKANIC ACID COMPOUNDS AND PROCEDURES FOR PRODUCING THEREOF | |
SE0104340D0 (en) | New compounds | |
NZ705710A (en) | Bicyclo[3.2.1]octyl amide derivatives and uses of same | |
CA2476065A1 (en) | Inhibitors of histone deacetylase | |
PT1077930E (en) | BENZAMIDE DERIVATIVES FOR THE TREATMENT OF DISEASES MEDIATED BY CYTOKINES | |
RU2002124522A (en) | 2-OXO-1-pyrrolidine derivatives, method for their preparation and use | |
WO2006034833A1 (en) | Cyclic diarly ureas suitable as tyrosine kinase inhibitors | |
SE0104334D0 (en) | Therapeutic agents | |
CA2264556A1 (en) | Substituted n-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides | |
GEP20053459B (en) | New Thiadiazoles and Oxidiazoles and Their Use as Phosphodiesterase-7 Inhibitors | |
FR2800735B1 (en) | NOVEL ARALKYL-1,2-DIAMINES HAVING CALCIMIMETIC ACTIVITY AND THEIR METHOD OF PREPARATION | |
BR0211559A (en) | Therapeutically useful compounds, tetracyclic binder compositions and their uses | |
NO932520D0 (en) | PREPARATION FOR HEALING THE DISEASE SJOEGREN'S SYNDROME | |
RU94046141A (en) | Substituted(arylalkoxybenzyl)aminopropaneamide derivatives, processes for preparation thereof, and pharmaceutical composition | |
KR910004597A (en) | 1- (pyridinylamino) -2-pyrrolidinone, preparation method thereof and use thereof as medicament | |
BR0212676A (en) | 5-ht ligand therapeutic compounds, pharmaceutical compositions comprising such compounds and their uses | |
HU9303082D0 (en) | Process for production of 3,4-dihydro-2(1h)-quinolyne-derivatives with neuroprotective action and of pharmaceutical compositions containing them as medical agent | |
RU2205829C2 (en) | Substituted derivative of cyclobutylamine, antibacterial agent and pharmaceutical composition based on thereof | |
ATE289583T1 (en) | STEREOISOMERS OF PROPYL-ISOPROPYLACETAMIDE, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING SAME | |
BR9813607A (en) | Compound, process for preparing the same, pharmaceutical composition, and process for treating a disease condition | |
WO1989001330A3 (en) | W-arylsulphonamidoalkanoic acids for treatment of thromboxane mediated diseases | |
ZA888663B (en) | Substituted derivatives of 20,21-dinoreburanamenine,their preparation process and the new intermediates thus obtained,their use as medicaments and the pharmaceutical compositions containing them |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |