EP0946551A2 - N-piperazin-1-ylphenyl-benzamide derives - Google Patents

N-piperazin-1-ylphenyl-benzamide derives

Info

Publication number
EP0946551A2
EP0946551A2 EP97954435A EP97954435A EP0946551A2 EP 0946551 A2 EP0946551 A2 EP 0946551A2 EP 97954435 A EP97954435 A EP 97954435A EP 97954435 A EP97954435 A EP 97954435A EP 0946551 A2 EP0946551 A2 EP 0946551A2
Authority
EP
European Patent Office
Prior art keywords
phenyl
methoxy
methylpiperazin
heterocyclic ring
compound according
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Withdrawn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
EP97954435A
Other languages
German (de)
English (en)
Inventor
Steven Mark Smithkline Beecham Pharm. Bromidge
Francis David Smithkline Beecham Pharm. King
Paul Adrian Smithkline Beecham Pharm. Wyman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SmithKline Beecham Ltd
Original Assignee
SmithKline Beecham Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from GBGB9626376.9A external-priority patent/GB9626376D0/en
Priority claimed from GBGB9700902.1A external-priority patent/GB9700902D0/en
Application filed by SmithKline Beecham Ltd filed Critical SmithKline Beecham Ltd
Publication of EP0946551A2 publication Critical patent/EP0946551A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • 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
    • A61P25/28—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2

Definitions

  • This invention relates to compounds having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of CNS disorders.
  • EPA 0 021 580 and EPA 0 076 072 describe sulphonamide derivatives which are disclosed as having antiarrhythmic activity.
  • a structurally distinct class of compounds has now been discovered, which have been found to have 5HTg receptor antagonist activity.
  • 5HTg receptor antagonists are believed to be of potential use in the treatment of certain CNS disorders such as anxiety, depression, epilepsy, obsessive compulsive disorders, migraine, Alzheimers disease (enhancement of cognitive memory), sleep disorders, 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 present invention therefore provides, in a first aspect, a compound of formula (I) or a salt thereof:
  • P is 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 Ci .galkenylene group;
  • R.1 is halogen, C ⁇ .
  • ⁇ alkyl optionally substituted by one or more halogen atoms, C ⁇ .gcycloalkyl, COCi ⁇ alkyl, C ⁇ _6alkoxy, OCF3, hydroxy, hydroxyCi . ⁇ alkyl, 6alkylamino or diC galkylamino, cyano or Rl is 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; n is 0, 1, 2, 3, 4, 5 or 6:
  • R2 is C ⁇ _6 alkyl or aryl C ⁇ . ⁇ alkyl
  • R3 is a group R ⁇ or together with R ⁇ forms a group (CH2)2 ⁇ or (CH2)3O or R 3 is linked to R ⁇ to form a group (CH2)2 or (CH2)3;
  • R 4 is -X(CH2)p-R 6 where X is a single bond, CH , O, NH or N-C i .6alkyl and p is 0 to 6 and R ⁇ is an optionally substituted 5- to 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from nitrogen, sulphur or oxygen, or R ⁇ is NR ⁇ RS where R 7 and R ⁇ are independently hydrogen, C ⁇ _6 alkyl or aryl Ci _6 alkyl; and R 5 is hydrogen, halogen, C ⁇ alkyl, C3_6cycloalkyl, COC ⁇ galkyl, Ci.galkoxy, hydroxy, hydroxyC i _6alkyl, hydroxyC i _6alkoxy, C 1.galkoxyC ⁇
  • Ci .g Alkyl groups may be straight chain or branched.
  • aryl includes phenyl and naphthyl.
  • P is a bicyclic heterocyclic ring suitable examples include benzothiophene, quinoline or isoquinoline.
  • Suitable 5 to 7-membered heterocyclic rings 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 atom. Suitable substituents for these rings include R$ groups as defined above.
  • P is phenyl, thiophene, benzothiophene or naphthyl.
  • R! is a 5-7 membered heterocyclic or bicyclic heterocyclic ring suitable examples include those given within the description of group P.
  • R! is halogen or Ci .4 alkyl optionally substituted by one or more halogens, for example methyl or CF3.
  • n 0, 1, 2 or 3, particularly 1 or 2.
  • R ⁇ is C ⁇ . alkyl, in particular methyl or ethyl.
  • R ⁇ is a group R ⁇ or together with R ⁇ forms a group (CH2)2O or
  • R 3 is linked to R 2 to form a group (CH 2 )2 or (CH 2 )3.
  • R 3 is a group R$ in particular hydrogen.
  • R 4 is meta with respect to the carboxamide linkage.
  • X is a bond
  • p is 0
  • R ⁇ is an optionally substituted 5- to 7-membered heterocyclic ring.
  • the heterocyclic rings can be linked to the remainder of the molecule via a carbon atom or, when present, a nitrogen atom.
  • Optional substituents for these rings, which can be present on carbon and/or nitrogen atoms include
  • Ci .galkyl in particular methyl. More preferably R 4 is an optionally substituted piperazine. Most preferably R 4 is N-methylpiperazine or piperazine.
  • R ⁇ is Ci _6alkoxy, most preferably methoxy.
  • R$ is para with respect to the amide group.
  • Particular compounds of the 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):
  • R , n, P, and A are as defined in formula (I) or protected derivatives thereof and L is a leaving group with a compound of formula (III):
  • R 2 , R3, R4 and R5 ⁇ Q as defined in formula (I) or protected derivatives thereof and optionally thereafter: • removing any protecting groups, • forming a pharmaceutically acceptable salt.
  • 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.
  • 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).
  • Compounds of formula (I) and their pharmaceutically acceptable salts have 5HT6 receptor antagonists are believed to be of potential use in the treatment of certain CNS disorders such as anxiety, depression, epilepsy, obsessive compulsive disorders, migraine, Alzheimers disease and enhancement of cognitive memory, 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 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 disorders such as LBS
  • 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.
  • the dose of the compound used in the treatment of the aforementioned disorders will vary in the usual way with the seriousness of the disorders, the weight of the sufferer, and other similar factors.
  • 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 glycol: dimethyl 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 drugs 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 .
  • the compounds of Examples all showed good selective 5-HT6 receptor antagonist activity, having pKi values above 7.0 at human cloned 5-HT6 receptors.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Cette invention concerne de nouveaux dérivés de carboxamide ayant une activité sur le système nerveux central (SNC), des procédés de préparation de ces nouveaux composés ainsi que leur utilisation en tant que médicaments.
EP97954435A 1996-12-19 1997-12-15 N-piperazin-1-ylphenyl-benzamide derives Withdrawn EP0946551A2 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB9626376 1996-12-19
GBGB9626376.9A GB9626376D0 (en) 1996-12-19 1996-12-19 Novel compounds
GB9700902 1997-01-17
GBGB9700902.1A GB9700902D0 (en) 1997-01-17 1997-01-17 Novel compounds
PCT/EP1997/007160 WO1998027058A2 (fr) 1996-12-19 1997-12-15 Nouveaux composes

Publications (1)

Publication Number Publication Date
EP0946551A2 true EP0946551A2 (fr) 1999-10-06

Family

ID=26310680

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97954435A Withdrawn EP0946551A2 (fr) 1996-12-19 1997-12-15 N-piperazin-1-ylphenyl-benzamide derives

Country Status (4)

Country Link
EP (1) EP0946551A2 (fr)
JP (1) JP2001506995A (fr)
CA (1) CA2274055A1 (fr)
WO (1) WO1998027058A2 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6159979A (en) * 1997-04-18 2000-12-12 Smithkline Beecham P.L.C. Bicyclic aryl or a bicyclic heterocyclic ring containing compounds having a combined 5HT1A, 5HT1B and 5HT1D receptor antagonistic activity
HUP0003073A3 (en) 1997-07-11 2002-10-28 Smithkline Beecham Plc Benzenesulfonamide derivatives, process for producing them and their use as medicines
GB9803411D0 (en) * 1998-02-18 1998-04-15 Smithkline Beecham Plc Novel compounds
US6194410B1 (en) 1998-03-11 2001-02-27 Hoffman-La Roche Inc. Pyrazolopyrimidine and pyrazolines and process for preparation thereof
BRPI9913542B8 (pt) * 1998-09-10 2021-05-25 Hoffmann La Roche derivados de dihidrobenzodioxina carboxamida e dihidrobenzodioxina cetona como antagonistas do receptor 5-ht4 bem como composição farmacêutica, processo para a preparação dos referidos derivados e uso dos mesmos
GB9820113D0 (en) 1998-09-15 1998-11-11 Merck Sharp & Dohme Therapeutic agents
BR0014279A (pt) * 1999-09-25 2002-05-21 Smithkline Beecham Plc Derivados de piperazina como antagonistas 5-ht1b
US7132546B2 (en) 2000-12-22 2006-11-07 Ishihara Sangyo Kaisha, Ltd. Aniline derivatives or salts thereof and cytokine production inhibitors containing the same
WO2002055012A2 (fr) 2001-01-16 2002-07-18 Astrazeneca Ab Composes heterocycliques therapeutiques
BR0206513A (pt) 2001-01-16 2004-01-06 Astrazeneca Ab Composição, métodos de tratamento de um ser humano ou animal que sofre de depressão, ansiedade generalizada, distúrbios da alimentação, demência, distúrbio do p nico, distúrbios do sono, distúrbios gastrointestinais, distúrbios motores, distúrbios endócrinos, vasoespasmo e disfunção sexual, uso de qualquer um dos compostos, composição farmacêutica, e, processo para preparar compostos
GB0106586D0 (en) * 2001-03-16 2001-05-09 Smithkline Beecham Plc Novel compounds
SE0103644D0 (sv) * 2001-11-01 2001-11-01 Astrazeneca Ab Therapeutic isoquinoline compounds
BR112012024380A2 (pt) 2010-03-25 2015-09-15 Glaxosmithkline Llc compostos químicos

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TW240217B (fr) * 1992-12-30 1995-02-11 Glaxo Group Ltd
GB2273930A (en) * 1992-12-30 1994-07-06 Glaxo Group Ltd Benzanilide derivatives
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WO1995004729A1 (fr) * 1993-08-06 1995-02-16 Smithkline Beecham Plc Derives amides employes comme antagonistes du recepteur 5ht1d
JPH09503773A (ja) * 1993-10-19 1997-04-15 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 ５ｈｔ−１ｄレセプター拮抗剤用のベンズアニリド誘導体
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Also Published As

Publication number Publication date
CA2274055A1 (fr) 1998-06-25
WO1998027058A2 (fr) 1998-06-25
JP2001506995A (ja) 2001-05-29
WO1998027058A3 (fr) 1998-08-20

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