EP1228066A2 - Sulfonamidderivate - Google Patents

Sulfonamidderivate

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Publication number
EP1228066A2
EP1228066A2 EP00974509A EP00974509A EP1228066A2 EP 1228066 A2 EP1228066 A2 EP 1228066A2 EP 00974509 A EP00974509 A EP 00974509A EP 00974509 A EP00974509 A EP 00974509A EP 1228066 A2 EP1228066 A2 EP 1228066A2
Authority
EP
European Patent Office
Prior art keywords
methyl
description
compound
group
chloro
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.)
Withdrawn
Application number
EP00974509A
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English (en)
French (fr)
Inventor
Steven Mark Smithkline Beecham Pharm. Bromidge
Halina T. SmithKline Beecham Phar. SERAFINOWSKA
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SmithKline Beecham Ltd
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SmithKline Beecham Ltd
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Filing date
Publication date
Application filed by SmithKline Beecham Ltd filed Critical SmithKline Beecham Ltd
Publication of EP1228066A2 publication Critical patent/EP1228066A2/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • 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
    • A61P25/06—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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/22—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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

Definitions

  • This invention relates to novel sulfonamide compounds having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of CNS disorders.
  • WO 98/27081 discloses sulfonamide compounds that possess 5-HTg receptor antagonist activity and which are claimed to be useful in the treatment of various CNS disorders.
  • WO 94/21619 and EP 0701819 both disclose a series of naphthalene derivatives that are claimed to be 5-HTJA receptor ligands.
  • the present invention therefore provides, in a first aspect, a compound of formula (I) or a pharmaceutically acceptable salt thereof:
  • A is a single bond, a Ci .galkylene or a C2-6 a lkenylene group
  • R! is halogen, C ⁇ . ⁇ alkyl optionally substituted by one or more halogen atoms, C3_6cycloalkyl, phenyl, COC galkyl, C ⁇ galkoxy, OCF3, hydroxy, hydroxyCi.galkyl, hydroxyC 1.galkoxy, Ci.galkoxyCi.galkoxy, nitro, amino, Ci .galkylamino or diCi _ ⁇ alkylamino;
  • R.2 is hydrogen, Ci. _6alkyl or together with a group R ⁇ forms a group -(CR6R7)p- where R6 and R? are independently hydrogen or Cj.galkyl and p is 2, 3 or 4;
  • R3 is C1. ⁇ alkyl optionally substituted by one or more halogen atoms, halogen, C1.
  • R2 forms a group -(CR ⁇ R ⁇ )p- as defined above; m is 0, 1 or 2; R4 is a group -X-R ⁇ where X is a single bond, CH2, O, NH or N-C j .galkyl and R ⁇ is an optionally substituted 5- to 7-membered heterocyclic ring or a bicyclic heterocyclic ring containing 1 to 3 heteroatoms selected from nitrogen, sulphur or oxygen; Q is a phenyl ring or is a 6 membered heteroaryl ring containing one or two nitrogen atoms.
  • C 1 -6alkyl 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 When P is naphthyl this is intended to denote both naphth-1-yl and naphth-2-yl groups.
  • P When P is a 5 or 6-membered heteroaryl ring suitable examples include thienyl, furyl, pyrrolyl, triazolyl, diazolyl, oxazolyl, thiazolyl, oxadiazolyl, isothiazolyl, isoxazolyl, thiadiazolyl, pyridyl, pyrimidyl and pyrazinyl.
  • P When P is a bicyclic heteroaryl ring suitable examples include indolyl, benzofiiryl, benzothienyl, quinolinyl and isoquinolinyl.
  • P When P is a tricyclic heteroaryl ring a preferred example is dibenzo furyl.
  • the heteroaryl rings can be linked to the remainder of the molecule via any suitable carbon atom or, when present, a nitrogen
  • P is phenyl, naphthyl, benzofiiryl or benzothienyl.
  • R1 When n is more than 1 the groups R1 can be the same or different.
  • R! is halogen (particular chloro or bromo), or a C ⁇ _6alkyl group optionally substituted by one or more halogen atoms, for example, methyl, ethyl, isopropyl, t-butyl or trifluoromethyl.
  • n 0, 1, 2 or 3, particularly 1 or 2.
  • R2 together with a group R ⁇ forms a further group -(CR6R7)p- both of the groups R6 and R are preferably hydrogen and p is preferably 2.
  • R ⁇ is preferably hydrogen.
  • a substituent R ⁇ can be attached at any unsubstituted carbon atom within the fused ring.
  • m is more than 1 the groups R ⁇ can be the same or different. It will be appreciated that when the R2/R3 groups are linked together, the group R ⁇ must be attached to one of the carbon atoms of the fused ring with an ortho relationship with respect to the sulfonamide linkage. Preferably m is 0.
  • the group R ⁇ can be attached at any unsubstituted carbon atom within the ring
  • R5 is a 5- to 7- membered heterocyclic ring
  • suitable examples include piperazinyl, piperidinyl, pyrrolidinyl and morpholinyl.
  • the 5- to 7- membered heterocyclic rings can be linked to the remainder of the molecule via a carbon atom or, when present, a suitable nitrogen atom.
  • X is O, NH or N-C j.galkyl then the 5- to 7- membered heterocyclic ring must be linked to the rest of the molecule via a carbon atom.
  • R5 is a bicyclic heterocyclic ring
  • Optional substituents for rings within the definition of R ⁇ which can be present on carbon and/or nitrogen atoms, include Cj.galkyl, in particular methyl.
  • R ⁇ is an unsubstituted piperazine or N-methyl piperazine attached to the rest of the molecule via a suitable nitrogen atom.
  • Q is a phenyl ring or is a 6 membered heteroaryl ring containing one or two nitrogen atoms.
  • Q together with the phenyl ring to which it is fused, forms a quinoline, isoquinoline or quinazoline ring.
  • Particular preferred compounds of this invention include:
  • 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 .
  • Compounds of formula (I) may also form solvates such as hydrates, and the invention also extends to these forms. When referred to herein, it is understood that the term 'compound of formula (I)' also includes these forms.
  • 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 the coupling of a compound of formula (II) or protected derivatives thereof:
  • Suitable leaving groups include halogen, in particular chloro.
  • the reaction of a compounds of formulae (II) and (III) is 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.
  • 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.
  • 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.
  • N-substituted piperazines can be prepared by acylation or alkylation of the appropriate NH-piperazine compound according to standard procedures.
  • compositions of formula (I) and their pharmaceutically acceptable salts may be prepared conventionally by reaction with the appropriate acid or acid derivative.
  • Compounds of formula (I) and their pharmaceutically acceptable salts have
  • 5-HTg 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. age related cognitive decline and/or Alzheimers disease), Parkinson's Disease, ADHD (attention deficit / hyperactivity disorder), sleep disorders (including disturbances of circadian rhythm), 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 spinal trauma and/or head injury such as hydrocephalus.
  • Compounds of the invention are also expected to be of use in the treatment of certain GI (gastrointestinal) disorders such as IBS (Irritable Bowel Syndrome).
  • 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 provides a compound of general formula (I) or a pharmaceutically acceptable salt for use in the treatment or prophylaxis of schizophrenia,
  • ADHD ADHD, cognitive memory enhancement, anxiety and/or depression.
  • 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 safe and 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 sterilisation 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.
  • 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.
  • 6-Nitroquinoline-l -oxide (24.5g, 0.13mmol) was added portionwise to ice-cooled , stirred phosphorus oxychloride (150ml). The mixture was then heated to reflux under argon for 3 hours to produce a precipitate. After cooling the mixture to room temperature, it was slowly poured onto stirred ice (1.5Kg) then with maintained cooling it was neutralised with 40% NaOH solution, resulting in a solid precipitating which was filtered and washed with water (6 x 200ml). The solid was dried at 60°C under vacuum to afford crude material which was purified by column chromatography over silica gel eluting with dichloromethane to give the following isomeric compounds:
  • N-Methylpiperazine (13ml, 0.17mol) was added dropwise to a stirred solution of 4- chloro-6-nitroquinazoline (Yakugaku Zasshi, 1974, 94(4), 417-423) (2.44g, 11. ⁇ mmol) in dry dichloromethane (60ml).
  • This compound was prepared from l-(4-chloro-phenylsulfanyl)-3-methyl-butan-2-one
  • Example 2 The following hydrochloride compounds (E8-E26) (Table 2) were prepared as described in Example 7 by reaction of the appropriate sulfonyl chloride derivative with 6-amino-4- (4- tert-butoxycarbonylpiperazin-l-yl)quinoline (D7).
  • the sulfonyl chloride used in the preparation of Example 9 is described in Description 24.
  • Other sulfonyl chlorides are prepared as indicated: Example 10 (D 16 and D 19), El 3 (D25), El 5 (D17 and D18), El 6 (D20 and D22), E17 (D21 and D23), E18 (D30 and D31), E21 (D36), E24 (D32 and D33), E25 (D34 and D35).
  • Example 27 l-(5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonyl)-8-(4-methyl-piperazin-l-yI)- 2,3-dihydro-lH-pyrrolo[2,3-g]quinoline Hydrochloride (E27)
  • E27 A solution of 5 -chloro-3 -methyl-benzothiophene-2-sulfonyl chloride (75mg, 0.27mmol) and 8-(4-methyl-piperazin-l-yl)-2,3-dihydro-lH-pyrrolo[2,3-g]quinoline (D17)(72mg, 0.27mmol) in 1,2-dichloroethane was refluxed for 5 hours under argon.
  • Example 4 The following hydrochloride compounds (E31-E34)(Table 4) were prepared as described in Example 7 by reaction of the appropriate sulfonyl chloride derivative with 6-amino-4- (4-tert-butoxycarbonylpiperazin-l-yl)-3 -methyl quinoline (D42).
  • the sulfonyl chloride used to prepare Example 33 is described in Descriptions D19 and D16.
  • the hydrochloride compounds (E36, E37)(Table 5) were prepared as described in Example 35 by reaction between the appropriate sulfonyl chloride and quinoline derivatives.
  • the hydrochloride compounds (E38-E41) were prepared as described in Example 7 and when appropriate the compounds were purified by column chromatography. The descriptions of the preparations of the quinoline derivatives used to derive these examples are indicated as follows: E36 (D44), E37 (D27), E38 (D47), E39 (D50), E40 (D57), E41 (D53).

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Addiction (AREA)
  • Hospice & Palliative Care (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Quinoline Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP00974509A 1999-11-05 2000-11-02 Sulfonamidderivate Withdrawn EP1228066A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9926302.2A GB9926302D0 (en) 1999-11-05 1999-11-05 Novel compounds
GB9926302 1999-11-05
PCT/EP2000/010911 WO2001032646A2 (en) 1999-11-05 2000-11-02 Sulfonamide derivatives

Publications (1)

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EP1228066A2 true EP1228066A2 (de) 2002-08-07

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EP (1) EP1228066A2 (de)
JP (1) JP2003513085A (de)
AU (1) AU1278701A (de)
GB (1) GB9926302D0 (de)
WO (1) WO2001032646A2 (de)

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