EP0883613A1 - Derives de sulfonamide en tant qu'antagonistes du recepteur de 5ht7 - Google Patents

Derives de sulfonamide en tant qu'antagonistes du recepteur de 5ht7

Info

Publication number
EP0883613A1
EP0883613A1 EP97902289A EP97902289A EP0883613A1 EP 0883613 A1 EP0883613 A1 EP 0883613A1 EP 97902289 A EP97902289 A EP 97902289A EP 97902289 A EP97902289 A EP 97902289A EP 0883613 A1 EP0883613 A1 EP 0883613A1
Authority
EP
European Patent Office
Prior art keywords
methyl
propyl
sulfonamide
methylpiperidin
alkyl
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Withdrawn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
EP97902289A
Other languages
German (de)
English (en)
Inventor
Ian Thomson-SmithKline Beecham Pharmace. FORBES
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 GBGB9602679.4A external-priority patent/GB9602679D0/en
Priority claimed from GBGB9613263.4A external-priority patent/GB9613263D0/en
Application filed by SmithKline Beecham Ltd filed Critical SmithKline Beecham Ltd
Publication of EP0883613A1 publication Critical patent/EP0883613A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • 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
    • C07D215/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/12—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • 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
    • C07D295/125—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • 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
    • 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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond

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 and other disorders.
  • 5HT7 receptor antagonists are believed to be of potential use in the treatment or prophylaxis of certain CNS disorders such as anxiety, depression, sleep disorders, migraine, Parkinson's disease, schizophrenia, pain, appetite disorders and other indications such as inflammation, spastic colon, renal disorders, hypotension, cardiovascular shock, septic shock and gastrointestinal diseases.
  • the present invention therefore provides, in a first aspect, use of a compound of formula (I) or a pharmaceutically acceptable salt thereof:
  • Ar is an optionally substituted mono- or bicyclic aromatic or heteroaromatic ring;
  • R 1 is Cj.6 alkyl;
  • R2 and R ⁇ are each independently hydrogen or Ci .g alkyl
  • R4 and R5 are independently hydrogen, C ⁇ . alkyl, arylC i .5 alkyl or aryl or together with the nitrogen atom to which they are attached form an optionally substituted 5- to
  • n 2 to 4 in the manufacture of a medicament for the treatment of disorders in which antagonism of the 5HT7 receptor is beneficial.
  • C j .g Alkyl groups may be straight chain or branched.
  • Ar is an optionally substituted mono- or bicyclic aromatic or heterocyclic ring.
  • Preferred aromatic rings include phenyl and naphthyl.
  • Preferred heteroaromatic groups include thiophene, quinoline and isoquinoline.
  • Optional substituents for aryl and heterocyclic groups include C ⁇ .
  • alkyl optionally substituted by NR 7 R 8 , C3.6 cycloalkyl, C3.6 cycloalkyi-C 1 _ ⁇ 5 alkyl, optionally substituted aryl, arylC ⁇ _6 alkyl, C2.6 aikenyl, C2-6 alkynyl, C1.6 alkylthio, cyano, nitro, halogen, CF3, C 2 F 5 , NR 7 R 8 , CONR 7 R 8 , NR 7 COR 8 , S(0) p NR 7 R 8 , CHO, OCF3, SCF3, COR 9 , CH 2 OR 9 , C0 2 R 9 or OR 9 where p is 1 or 2 and R 7 , R 8 and R 9 are independently hydrogen, Cj.g alkyl, optionally substituted aryl or optionally substituted arylCi .galkyl;
  • Ar is a naphthyl group, a substituted phenyl group, or a dibromothienyl group.
  • R 1 is C ⁇ . alkyl.
  • R 1 groups include methyl and ethyl groups.
  • R ⁇ is methyl.
  • R- and R 3 are independently hydrogen or C j .g alkyl.
  • R 2 and R3 are hydrogen or methyl. More preferably one of R 2 and R ⁇ is hydrogen and the other is methyl attached to the carbon atom of the side chain adjacent to the sulfonamide nitrogen.
  • R ⁇ and R ⁇ are independently hydrogen, C j .g alkyl or together with the nitrogen atom to which they are attached form an optionally substituted 5- to 8- membered heterocyclic ring optionally containing a further heteroatom selected from nitrogen or oxygen.
  • R ⁇ and R ⁇ form an optionally substituted 5- to 8- membered heterocyclic ring, in particular an optionally substituted 6-membered ring.
  • Optional substituents for such rings, which can be present on carbon and nitrogen atoms can be selected from suitable groups listed above and include Cj .5 alkyl.
  • R ⁇ and R* form a piperidine ring substituted by a methyl group.
  • n 2 to 4.
  • n 3;
  • Ar is a naphthyl group, a substituted phenyl group, or a dibromothienyl group and R 10 is hydrogen, C ⁇ . ⁇ alkyl, cycloC _6 alkyl, arylC ⁇ _6 alkyl, CF3, C2F5 or
  • Particularly preferred compounds of the invention include: N-Methy l-N-[ 1 -methyI-3-(3-methylpiperidin- 1 -y l)propyl]- 1 -naphthalenesulfonamide,
  • N-Methyl-N-(4-piperidin- 1 -yl-butyl)- 1 -naphthalene sulfonamide N-Methyl-N-[lR-methyl-3-(4-methylpiperidin-l-yl)propyl]-3,4-dibromobenzene sulfonamide,
  • Other preferred compounds of the invention include those of examples 29 - 83 which are disclosed herein.
  • 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.
  • 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 (a) the coupling of a compound of formula (II):
  • R 2 and R J are as defined in formula (I), R ⁇ ' and R ⁇ ' are R ⁇ and R ⁇ respectively or protected derivatives thereof, and R6 is R* or hydrogen; or (b) coupling a compound of formula (IN):
  • Suitable leaving groups L include halogen, in particular chloro.
  • the reaction of a compounds of formulae (II) and (III) is preferably carried out in an inert solvent such as dichloromethane optionally in the presence of a base such as triethylamine.
  • suitable leaving groups L include halogen, in particular chloro.
  • Suitable reducing agents include lithium aluminium hydride. Those skilled in the art will appreciate that it may be necessary to protect R 4 and R ⁇ groups. 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.
  • R When R is hydrogen it can be converted to a group R* using standard alkylation procedures, for example by reaction with an alkyl halide in the presence of a base such as sodium hydride.
  • compositions may be prepared conventionally by reaction with the appropriate acid or acid derivative.
  • Compounds of formula (I) and their pharmaceutically acceptable salts have 5 5HT7 receptor antagonist activity and are believed to be of potential use for the treatment or prophylaxis of certain CNS disorders such as anxiety, depression, sleep disorders, migraine, Parkinson's disease, schizophrenia, pain, appetite disorders and other indications such as inflammation, spastic colon, renal disorders, hypotension, cardiovascular shock, septic shock and gastrointestinal diseases. 0 .
  • the compounds of the invention are used to treat CNS diseases.
  • the invention also provides a compound of formula (i) and preferably a compound of formula (ii) 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 present invention also provides a pharmaceutical composition, which comprises a compound of formula (i) and preferably a compound of formula (ii) 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 in preparing solutions, 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.
  • 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.
  • the title compound was prepared from D13 in a similar way to D7 (1.lg, 78%).
  • the title compound was prepared from D14 in a similar way to D8 (0.7 lg, 87%).
  • the title compound was prepared using 3(R)methylpiperidine and a procedure similar to that in D5, D6 and E2.
  • the title compound was prepared in a similar way to E4 using Dl 5 (350 mg, 2 mmol), triethylamine (0.28 ml, 2 mmol) and 1-naphthalenesulfonyl chloride (0.46g, 64%).
  • the title compound was prepared from D15 (1 15 mg, 0.67 mmol) triethylamine (90 ⁇ l, 0.67 mmol) and benzenesulfonyl chloride (86 ⁇ l, 0.67 mmol) using a similar procedure to E4 (50 mg, 24%).
  • the title compound was prepared from D15 (1 15 mg, 0.67 mmol), triethylamine (90 ⁇ l, 0.67 mmol) and 2-naphthalenesulfonyl chloride (153 mg, 0.67 mmol) using a similar procedure to E4 (132 mg, 55%).
  • Example 9 The procedure of Example 9 was employed.
  • the reagents used were: l-(3- methylamino butyl)-2(R)-methyipiperidine, 4,5-dibromo-2-thiophenesulphonyl chloride and diisopropylethylamine.
  • the title compound was prepared using 4-methylpiperidine and 2,3- dibromothiophene-5-sulphonyl chloride in the methods described in D5, D6 and E2.
  • the title compound was prepared using 4-methylpiperidine and 3,4-dichlorophenyl sulphonyl chloride in the methods described in D5, D6 and E2.
  • the title compound was prepared using 1 -phenyipiperazine and 1 -naphthylsulphonyl chloride in the methods described in D5, D6 and E2.
  • the title compound was prepared using 1 -phenyl piperazine and 2,3- dibromothiophene-5-sulphonyl chloride in the methods described in D5, D6 and E2.
  • Example 9 The procedure of Example 9 was employed.
  • the reagents used were: l -[3- methylamino-3(R)-methylpropyl]-4-methylpiperidine, 3,4-dibromobenzenesulphonyi chloride and diisopropylethylamine.
  • Ci 7H26Br2N ⁇ 2S+H requires 483
  • Examples 21-28 were prepared by shaking a 1 : 1 mixture of the appropriate aryl sulphonyl chloride with the appropriate secondary amine in dichloromethane. After lOh, the resultant precipitate was filtered off and dried.
  • Ci4H2iN2 ⁇ 2SBr+H requires 361 and 363
  • Examples 29-83 were prepared by the following generic procedure.
  • the title compound was prepared using 4-methylpiperidine and 3-bromo-4- chlorophenyl sulfonyl chloride in the methods described in D5, D6 and E2.
  • the affinity of test drugs for the 5-HT 7 receptor binding site can be determined by assessing their ability to displace [ ⁇ H]-5-carboxamidotryptamine from 5-HT 7 receptor clones expressed in 293 cells (To et al., 1995 and Sleight et al., 1995).
  • the cells suspension 400 ⁇ l was incubated with [ ⁇ H]-5-carboxamido- tryptamine (0.5nM) in Tris HCl buffer (pH 7.4) at 37°C for 45mins. Non-specific binding was measured in the presence of 5 -hydroxy tryptamine
  • test drug (10 * 1 1 to 10' ⁇ M final concentration) were added in a volume of 50ul. The total assay volume was 500 ⁇ l. Incubation was stopped by rapid filtration using a Tomtec cell harvester and radioactivity measured by scintillation counting on a Packard Topcount. The IC50 values and pKi values were calculated by INFLEXION, a non-linear iterative curve fitting programme based in EXCEL (Bowen and Jerman. 1994).

Abstract

L'invention concerne des composés présentant une activité d'antagonistes de 5HT7, des procédés servant à les préparer, des compositions les contenant, ainsi que leur utilisation dans le traitement de maladies du système nerveux central et d'autres maladies.
EP97902289A 1996-02-09 1997-01-27 Derives de sulfonamide en tant qu'antagonistes du recepteur de 5ht7 Withdrawn EP0883613A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB9602679 1996-02-09
GBGB9602679.4A GB9602679D0 (en) 1996-02-09 1996-02-09 Novel compounds
GB9613263 1996-06-25
GBGB9613263.4A GB9613263D0 (en) 1996-06-25 1996-06-25 Novel compounds
PCT/EP1997/000446 WO1997029097A1 (fr) 1996-02-09 1997-01-27 Derives de sulfonamide en tant qu'antagonistes du recepteur de 5ht¿7?

Publications (1)

Publication Number Publication Date
EP0883613A1 true EP0883613A1 (fr) 1998-12-16

Family

ID=26308647

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97902289A Withdrawn EP0883613A1 (fr) 1996-02-09 1997-01-27 Derives de sulfonamide en tant qu'antagonistes du recepteur de 5ht7

Country Status (3)

Country Link
EP (1) EP0883613A1 (fr)
JP (1) JP2000504677A (fr)
WO (1) WO1997029097A1 (fr)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
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EP0994862B1 (fr) 1997-07-11 2005-06-01 SmithKline Beecham plc Derives sulphonamide comme antagonistes du recepteur 5-ht6 et procede pour leur preparation
CA2296314A1 (fr) * 1997-07-25 1999-02-04 Merck & Co., Inc. Amines cycliques modulant l'activite des recepteurs de chimiokines
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GB9906624D0 (en) 1999-03-23 1999-05-19 Smithkline Beecham Plc Novel compounds
WO2000069437A1 (fr) 1999-05-18 2000-11-23 Synaptic Pharmaceutical Corporation Utilisation d'agonistes ou d'antagonistes vis-a-vis du recepteur 5-ht7 pour traiter les troubles de la vessie
GB9912701D0 (en) * 1999-06-01 1999-08-04 Smithkline Beecham Plc Novel compounds
ITMI20011412A1 (it) * 2001-07-04 2003-01-04 Consiglio Nazionale Ricerche Nuovi diazoderivati e processo per la loro preparazione
ITMI20011413A1 (it) * 2001-07-04 2003-01-04 Consiglio Nazionale Ricerche Metodo di trattamento conservativo di materiale cartaceo
GB0128885D0 (en) 2001-12-03 2002-01-23 Merck Sharp & Dohme Therapeutic agents
EP1676844A1 (fr) 2004-12-28 2006-07-05 Laboratorios Del Dr. Esteve, S.A. Antagonistes de recepteurs 5-HT7
US7928121B2 (en) 2002-02-19 2011-04-19 Laboratorios Del Dr. Esteve, S.A. 5-HT7 receptor antagonists
US7553965B2 (en) 2002-11-07 2009-06-30 Laboratories Del Dr. Esteve, S.A. 5-HT7 receptor antagonists
EP1676840A1 (fr) 2004-12-28 2006-07-05 Laboratorios Del Dr. Esteve, S.A. Antagonists du recepteur 5-HT7
GB0311201D0 (en) 2003-05-15 2003-06-18 Merck Sharp & Dohme Therapeutic agents
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EP1630158A1 (fr) * 2004-08-18 2006-03-01 Laboratorios Del Dr. Esteve, S.A. Antagonistes des recepteurs 5-HT7
ES2257167B1 (es) * 2004-08-18 2007-06-01 Laboratorios Del Dr Esteve, S.A. Inhibidores del receptor 5-ht7.
ES2257168B1 (es) * 2004-08-18 2007-06-01 Laboratorios Del Dr Esteve, S.A. Ligandos del receptor 5-ht7.
EP1885693A4 (fr) * 2005-05-18 2010-09-15 Siegfried Wurster Peptidomimetiques a haute selectivite pour les sous-types 1 et/ou 4 des recepteurs de la somatostatine
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EP2149373A1 (fr) 2008-08-01 2010-02-03 Laboratorios Del. Dr. Esteve, S.A. Ligands du récepteur 5HT7 et compositions les comprenant
EP2151777A1 (fr) 2008-08-01 2010-02-10 Laboratorios Del. Dr. Esteve, S.A. Procédé de criblage des ligands du récepteur 5HT7 basé sur un nouveau modèle pharmacophore et filtre de profil de descripteur
US8883796B2 (en) 2013-02-08 2014-11-11 Korea Institute Of Science And Technology Biphenyl derivatives, pharmaceutical composition comprising the same, and preparation method thereof
US9663464B2 (en) 2015-02-24 2017-05-30 Korea Institute Of Science And Technology Carbazole derivatives acting on 5-HT7 receptor
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