WO1999042465A2 - Sulphonamide derivatives being 5-ht6 receptor antagonists and process for their preparation - Google Patents
Sulphonamide derivatives being 5-ht6 receptor antagonists and process for their preparation Download PDFInfo
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- WO1999042465A2 WO1999042465A2 PCT/EP1999/001013 EP9901013W WO9942465A2 WO 1999042465 A2 WO1999042465 A2 WO 1999042465A2 EP 9901013 W EP9901013 W EP 9901013W WO 9942465 A2 WO9942465 A2 WO 9942465A2
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- 0 C*(CCC*1)*(C)C2N(C)CCC1(C)NC2 Chemical compound C*(CCC*1)*(C)C2N(C)CCC1(C)NC2 0.000 description 4
- YKBHIAMXELZBES-UHFFFAOYSA-N CN1C(CC2)CN2CC1 Chemical compound CN1C(CC2)CN2CC1 YKBHIAMXELZBES-UHFFFAOYSA-N 0.000 description 1
- ATVTWWYYPPINDG-UHFFFAOYSA-N CN1C(CCC2)CN2CC1 Chemical compound CN1C(CCC2)CN2CC1 ATVTWWYYPPINDG-UHFFFAOYSA-N 0.000 description 1
- ATZWXDWXCISHBE-UHFFFAOYSA-N CN1CC(CCC2)N2CC1 Chemical compound CN1CC(CCC2)N2CC1 ATZWXDWXCISHBE-UHFFFAOYSA-N 0.000 description 1
- WGXIYIFYMGDZJY-UHFFFAOYSA-N CN1CC(CCCC2)N2CC1 Chemical compound CN1CC(CCCC2)N2CC1 WGXIYIFYMGDZJY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- 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
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- 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
- A61P25/08—Antiepileptics; Anticonvulsants
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
- A61P25/32—Alcohol-abuse
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- 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
- A61P25/34—Tobacco-abuse
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Definitions
- This invention relates to novel sulphonamide compounds having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of CNS disorders.
- US patent 5,703,072 discloses bicyclic nonane and decane compounds having dopamine receptor affinity which are claimed to be of use in the treatment of schizophrenia.
- US patent 5,457,121 discloses cis-hexahydro-5-( 1,2,3, 4-Tetrahydro-2- naphthalenyl)pyrrolo ⁇ 3,4,c>pyrroles as inhibitors of serotonin reuptake.
- European patent application EP 0815861 discloses a series of aryl sulphonamide compounds that are said to possess 5-HT6 receptor activity and are useful in the treatment of various CNS disorders. A structurally distinct class of compounds has now been discovered, which have been found to have 5-HTg receptor antagonist activity.
- the present invention therefore provides, in a first aspect, a compound of formula (I) or a salt thereof:
- E is -SO 2 NH- or -NHSO 2 -
- P is a phenyl, naphthyl, a bicyclic heterocyclic ring or is a 5 to 7-membered heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulphur;
- A is a single bond, a C ⁇ .galkylene or a Cj.galkenylene group;
- R.1 is halogen, C ⁇ alkyl optionally substituted by one or more fluorine atoms, C3. gcycloalkyl, C ⁇ .galkoxy, OCF3, C ⁇ galkoxyC galkoxy, Ci. ⁇ alkanoyl, amino, alkylamino or dialkylamino, SR.11 where R.11 is hydrogen or C ⁇ _6alkyl or R* is phenyl, benzyl, naphthyl, a bicyclic heterocyclic ring or is a 5 to 7-membered heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulphur; and n is O, 1, 2, 3, 4 or 5;
- R.3 is a group R ⁇ or together with R ⁇ forms a group (CH.2)2 ⁇ or (CH.2)3 ⁇ ;
- R4 is selected from a group of formula (i), (ii) or (iii): Formula (i)
- R" is C ⁇ alkyl optionally substituted by one or more halogen atoms; m is 0, 1 or 2; q is 0, 1, 2, 3 or 4; or
- R ⁇ and q are as defined in formula (I) and R ⁇ is hydrogen or C ⁇ alkyl;
- R5 is hydrogen, halogen, C ⁇ . ⁇ alkyl, C ⁇ .galkoxy optionally substituted with one or more fluorine atoms, trifluoromethyl, or together with R ⁇ forms a group (CH.2)2 ⁇ or (CH 2 ) 3 O.
- Alkyl groups may be straight chain or branched.
- the term 'halogen' is used herein to describe, unless otherwise stated, a group selected from fluorine, chlorine, bromine or iodine.
- P is a bicyclic heterocyclic ring
- suitable examples include benzothienyl, indolyl, quinolinyl or isoquinolinyl.
- P is a 5 to 7-membered heterocyclic ring
- suitable examples include thienyl, furyl, pyrrolyl, triazolyl, diazolyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, isothiazolyl, isoxazolyl, thiadiazolyl, pyridyl, pyrimidyl, pyrrolidinyl and pyrazinyl.
- the heterocyclic rings can be linked to the remainder of the molecule via any suitable carbon atom or, when present, a nitrogen.
- P is phenyl, naphthyl, thienyl and most preferably benzothienyl,
- A is a single bond or methylene.
- R is hydrogen, halogen, phenyl, C ⁇ . ⁇ alkoxy most preferably OMe, SRI 1 most preferably SMe or Cj.galkyl optionally substituted by one or more fluorine atoms, for example methyl or trifluoromethyl.
- R! is a heterocyclic group suitable examples include those listed above for P.
- n is 1, 2 or 3.
- R ⁇ is a group R ⁇ , in particular hydrogen.
- R ⁇ is a group:
- R ⁇ is C ⁇ alkoxy, most preferably methoxy.
- R ⁇ is para with respect to the sulphonamide linkage.
- Particularly preferred compounds of the invention include 5 -Chloro-3 -methylbenzo [ ⁇ ]thiophene-2-sulphonic acid[4-methoxy-3 - (octahydropyrido[l,2- ⁇ ]pyrazin-2-yl) phenyl] amide,
- the compounds of the formula (I) can form acid addition salts with acids, such as conventional pharmaceutically acceptable acids, for example maleic, hydrochloric, hydrobromic, phosphoric, acetic, fumaric, salicylic, citric, lactic, mandelic, tartaric and methanesulphonic.
- acids such as conventional pharmaceutically acceptable acids, for example maleic, hydrochloric, hydrobromic, phosphoric, acetic, fumaric, salicylic, citric, lactic, mandelic, tartaric and methanesulphonic.
- Certain compounds of formula (I) are capable of existing in stereoisomeric forms including diastereomers and enantiomers and the invention extends to each of these stereoisomeric forms and to mixtures thereof including racemates.
- the different stereoisomeric forms may be separated one from the other by the usual methods, or any given isomer may be obtained by stereospecific or asymmetric synthesis.
- the invention also extends to any tautomeric forms and mixtures thereof.
- the present invention also provides a process for the preparation of a compound of formula (I) or a pharmaceutically acceptable salt thereof, which process comprises:
- R ⁇ , R4 and R ⁇ are as defined in formula (I) and L is a leaving group
- Rl , P, n and A are defined in formula (I) and L is a leaving group with a compound of formula (V) or protected derivatives thereof:
- Suitable leaving groups include halogen such as chloro or bromo, in particular chloro.
- the reactions of compounds of formula (II) and (III) and that of compounds of formula (IV) and (V) are typically carried out by mixing the two reagents together, optionally in an inert solvent such as dichloromethane or acetone. Such a reaction may be carried out in the presence of base.
- Suitable protecting groups and methods for their attachment and removal are conventional in the art of organic chemistry, such as those described in Greene T.W. 'Protective groups in organic synthesis' New York, Wiley (1981).
- suitable protecting groups for the piperazine group include BOC, COCCI3 , COCF3 and methyl the latter of which may be removed by treatment with 1- chloroethyl chloroformate according to standard procedures.
- a compound of formula (III) (in which R ⁇ is a group of formula (iii)), that is, 4-methoxy-3 -(5-methyl-cw-hexahydropyrrolo [3 ,4-c]pyrrolo-2-yl)-benzenesulfony 1 chloride can be prepared by coupling cz ' .y-hexahydro-2-methylpyrrolo[3,4-c]pyrrole hydrochloride (US 5,457,121) with 2-bromoanisole using a palladium coupling reaction according to the general methodology disclosed by Buchwald (Tet. Lett. 1997, 38, 6359-6362). The resulting amine can be treated with chlorosulfonic acid in dichloromethane to give the required compound.
- Aryl octahydropyrido[l,2-tf]pyrazines of formula (V) (in which R ⁇ is a group of formula (i)), can be obtained by a synthetic procedure as represented by scheme 1.
- compositions may be prepared conventionally by reaction with the appropriate acid or acid derivative.
- 5HTg receptor antagonist activity and are believed to be of potential use in the treatment of certain CNS disorders such as anxiety, depression, epilepsy, obsessive compulsive disorders, migraine, cognitive memory disorders e g. Alzheimers disease, Parkinson' Disease, ADHD (Attention Deficit Disorder/Hyperactivity Syndrome), sleep disorders (including disturbances of Circadian rhythym), feeding disorders such as anorexia and bulimia, panic attacks, withdrawal from drug abuse such as cocaine, ethanol, nicotine and benzodiazepines, schizophrenia, and also disorders associated with spmal trauma and/or head injury such as hydrocephalus.
- CNS disorders such as anxiety, depression, epilepsy, obsessive compulsive disorders, migraine, cognitive memory disorders e g. Alzheimers disease, Parkinson' Disease, ADHD (Attention Deficit Disorder/Hyperactivity Syndrome), sleep disorders (including disturbances of Circadian rhythym), feeding disorders such as anorexia and bulimia, panic attacks, withdrawal from drug
- the invention also provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, for use as a therapeutic substance, in particular in the treatment or prophylaxis of the above disorders.
- the invention further provides a method of treatment or prophylaxis of the above disorders, in mammals including humans, which comprises administering to the sufferer a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof
- the invention provides the use of a compound of formula (I) or a pharmaceutically acceptable salt thereof in the manufacture of a medicament for the treatment or prophylaxis of the above disorders.
- the present invention also provides a pharmaceutical composition, which comprises a compound of formula (I) or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
- a pharmaceutical composition of the invention which may be prepared by admixture, suitably at ambient temperature and atmospheric pressure, is usually adapted for oral, parenteral or rectal administration and, as such, may be in the form of tablets, capsules, oral liquid preparations, powders, granules, lozenges, reconstitutable powders, injectable or infusable solutions or suspensions or suppositories. Orally administrable compositions are generally preferred.
- Tablets and capsules for oral administration may be in unit dose form, and may contain conventional excipients, such as binding agents, fillers, tabletting lubricants, disintegrants and acceptable wetting agents.
- the tablets may be coated according to methods well known in normal pharmaceutical practice.
- Oral liquid preparations may be in the form of, for example, aqueous or oily suspension, solutions, emulsions, syrups or elixirs, or may be in the form of a dry product for reconstitution with water or other suitable vehicle before use.
- Such liquid preparations may contain conventional additives such as suspending agents, emulsifying agents, non-aqueous vehicles (which may include edible oils), preservatives, and, if desired, conventional flavourings or colourants.
- fluid unit dosage forms are prepared utilising a compound of the invention or pharmaceutically acceptable salt thereof and a sterile vehicle.
- the compound depending on the vehicle and concentration used, can be either suspended or dissolved in the vehicle.
- the compound can be dissolved for injection and filter sterilised before filling into a suitable vial or ampoule and sealing.
- adjuvants such as a local anaesthetic, preservatives and buffering agents are dissolved in the vehicle.
- the composition can be frozen after filling into the vial and the water removed under vacuum.
- Parenteral suspensions are prepared in substantially the same manner, except that the compound is suspended in the vehicle instead of being dissolved, and sterilization cannot be accomplished by filtration.
- the compound can be sterilised by exposure to ethylene oxide before suspension in a sterile vehicle.
- a surfactant or wetting agent is included in the composition to facilitate uniform distribution of the compound.
- the composition may contain from 0.1% to 99% by weight, preferably from 10 to 60% by weight, of the active material, depending on the method of administration.
- suitable unit doses may be 0.05 to 1000 mg, more suitably 0.05 to 20.0 mg, for example 0.2 to 5 mg; and such unit doses may be administered more than once a day, for example two or three a day, so that the total daily dosage is in the range of about 0.5 to 100 mg; and such therapy may extend for a number of weeks or months.
- test compounds were dissolved in polyethylene glycokdimethyl sulphoxide (1 : 1) at 1 or lOmM and diluted to O.lmM using 5mM tris buffer (pH 7.7 @ 25°C). Dissolution was assisted by addition of 0.02ml 5M HC1 plus heating to 40°C and sonication for 10 minutes. Serial dilutions of test compounds in the same buffer were carried out using either a TECAN 5052 or Biomek 2000 Workstation.
- Samples of the diluted test compounds (0.05ml) were mixed with 0.05ml of radio-ligand [ 3 H]-LSD prepared in the incubation buffer, and 0.4ml of a suspension of a preparation of the washed membranes of HeLa_5HT6 cells (acquired from Dr. D. Sibley. NIH, Bethesda, see Ref l)(see Table 1), also in the incubation buffer.
- the details of the incubation conditions for each assay are shown in Table 2.
- the incubation buffer was 50mM Trizma (Sigma, UK) pH7.7 @ 25°C, 4mM MgCl 2 .
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99910228A EP1066288A2 (en) | 1998-02-18 | 1999-02-12 | Novel compounds |
JP2000532417A JP2002504484A (en) | 1998-02-18 | 1999-02-12 | New compound |
CA002321278A CA2321278A1 (en) | 1998-02-18 | 1999-02-12 | Novel compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9803411.9A GB9803411D0 (en) | 1998-02-18 | 1998-02-18 | Novel compounds |
GB9803411.9 | 1998-02-18 |
Publications (2)
Publication Number | Publication Date |
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WO1999042465A2 true WO1999042465A2 (en) | 1999-08-26 |
WO1999042465A3 WO1999042465A3 (en) | 1999-09-30 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/EP1999/001013 WO1999042465A2 (en) | 1998-02-18 | 1999-02-12 | Sulphonamide derivatives being 5-ht6 receptor antagonists and process for their preparation |
Country Status (5)
Country | Link |
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EP (1) | EP1066288A2 (en) |
JP (1) | JP2002504484A (en) |
CA (1) | CA2321278A1 (en) |
GB (1) | GB9803411D0 (en) |
WO (1) | WO1999042465A2 (en) |
Cited By (47)
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WO2001032659A1 (en) * | 1999-11-05 | 2001-05-10 | Smithkline Beecham P.L.C. | Isoquinoline and quinazoline derivatives for the treatment of cns disorders |
WO2002008179A1 (en) * | 2000-07-21 | 2002-01-31 | Biovitrum Ab | Aryl sulfonamides as serotonin antagonist for the treatment of obesity |
WO2002008178A1 (en) * | 2000-07-21 | 2002-01-31 | Biovitrum Ab | New combination of serotonin agonist (5ht2) and antagonist (5ht6)as pharmaceutical formulation |
WO2002018358A1 (en) * | 2000-08-31 | 2002-03-07 | Smithkline Beecham P.L.C. | N-(3,5-dichloro-2-methoxyphenyl)-4-methoxy-3-piperazin-1-yl-benzenesulfonamide |
WO2002022595A1 (en) * | 2000-09-18 | 2002-03-21 | Toa Eiyo Ltd. | N-substituted benzothiophenesulfonamide derivatives |
US6399617B1 (en) | 2000-07-21 | 2002-06-04 | Biovitrum Ab | Use |
WO2002092585A1 (en) * | 2001-05-11 | 2002-11-21 | Biovitrum Ab | Novel, arylsusfonamide compounds for the treatment of obesity, type ii diabetes and cns-disorders |
WO2002100822A1 (en) | 2001-06-11 | 2002-12-19 | Biovitrum Ab | Substituted sulfonamide compounds, process for their use as medicament for the treatment of cns disorders, obesity and type ii diabetes |
WO2003039547A1 (en) * | 2001-11-09 | 2003-05-15 | Biovitrum Ab | Use of sulfonamide derivatives in the treatment of obesity or for the reduction of food intake |
US6579870B2 (en) | 2000-06-20 | 2003-06-17 | Pharmacia & Upjohn Company | Bis-arylsulfones |
US6586592B2 (en) | 2000-06-20 | 2003-07-01 | Pharmacia & Upjohn Company | Bis-arylsulfones |
WO2003078419A1 (en) * | 2002-03-15 | 2003-09-25 | Toa Eiyo Ltd. | N-substituted benzothiophenesulfonamide derivative |
WO2004024729A1 (en) * | 2002-09-10 | 2004-03-25 | Pfizer Products Inc. | Diazabicyclic compounds useful in the treatment of cns and other disorders |
US6825202B2 (en) | 2001-08-10 | 2004-11-30 | Syntex (U.S.A.) Llc | Arylsulfonyl derivatives with 5-HT6 receptor affinity |
FR2865208A1 (en) * | 2004-01-16 | 2005-07-22 | Sanofi Synthelabo | New 4-heterocyclylcarbonyl-diazabicyclo-octane derivatives, useful for treating e.g. cognitive, neurological or psychiatric disorders, are selective ligands for the alpha7 subunit of nicotinic receptors |
WO2005074940A1 (en) * | 2004-02-04 | 2005-08-18 | Neurosearch A/S | Diazabicyclic aryl derivatives as cholinergic receptor modulators |
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US7071220B2 (en) | 2000-09-18 | 2006-07-04 | Toa Eiyo Ltd. | N-substituted benzothiophenesulfonamide derivatives |
EP1676841A1 (en) * | 2004-12-30 | 2006-07-05 | Esteve Laboratorios Dr. Esteve S.A. | Substitited indazolyl sulfonamide and 2,3-dihydro-indolyl sulfonamide compounds, their prepartion and use in medicaments |
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US7381728B2 (en) | 2004-07-28 | 2008-06-03 | Glaxo Group Limited | Piperazine derivatives useful for the treatment of gastrointestinal disorders |
US7420055B2 (en) | 2002-11-18 | 2008-09-02 | Chemocentryx, Inc. | Aryl sulfonamides |
US7452888B2 (en) | 2002-03-27 | 2008-11-18 | Glaxo Group Limited | Quinoline derivatives and their use as 5-ht6 ligands |
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US7662812B2 (en) | 2005-02-16 | 2010-02-16 | Neurosearch A/S | Diazabicyclic aryl derivatives and their use as chinolinergic ligands at nicotinic acetylcholine receptors |
WO2010032258A1 (en) | 2008-09-17 | 2010-03-25 | Suven Life Sciences Limited | Aryl sulfonamide amine compounds and their use as 5-ht6 ligands |
US7713978B2 (en) | 2006-03-31 | 2010-05-11 | Nigel Paul King | Compounds |
US7718650B2 (en) | 2001-05-11 | 2010-05-18 | Biovitrum Ab | Aryl sulfonamide compounds for treating obesity |
US7741519B2 (en) | 2007-04-23 | 2010-06-22 | Chemocentryx, Inc. | Bis-aryl sulfonamides |
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Also Published As
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WO1999042465A3 (en) | 1999-09-30 |
JP2002504484A (en) | 2002-02-12 |
EP1066288A2 (en) | 2001-01-10 |
GB9803411D0 (en) | 1998-04-15 |
CA2321278A1 (en) | 1999-08-26 |
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