WO1998050343A2 - (hetero)aryl carboxamide derivatives, process for their preparation and their use in the treatment of cns disorders - Google Patents
(hetero)aryl carboxamide derivatives, process for their preparation and their use in the treatment of cns disorders Download PDFInfo
- Publication number
- WO1998050343A2 WO1998050343A2 PCT/EP1998/002266 EP9802266W WO9850343A2 WO 1998050343 A2 WO1998050343 A2 WO 1998050343A2 EP 9802266 W EP9802266 W EP 9802266W WO 9850343 A2 WO9850343 A2 WO 9850343A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- formula
- oxygen
- hydrogen
- nitrogen
- Prior art date
Links
Classifications
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/75—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
Definitions
- the present invention relates to novel urea derivatives processes for their preparation, and pharmaceutical compositions containing them.
- WO 95/15954, WO 95/17398, WO 95/26328 and WO 96/06079 disclose a series of piperazine derivatives which are said to possess 5HT ⁇ rj> receptor antagonist activity. These compounds are alleged to be of use in the treatment of various CNS disorders such as depression.
- EPA 0533266/7/8 disclose a series of benzanilide derivatives which are said to possess 5-HTipj receptor antagonist activity.
- the present invention therefore provides a compound of formula (I) or a salt thereof:
- R a is a group of formula (i)
- R 1 is hydrogen, halogen, C ⁇ .galkyl, C3_6cycloalkyl, COCi.galkyl, C ⁇ _6 lkoxy, hydroxy, hydroxyCi ⁇ alkyl, hydroxyC ⁇ _6alkoxy, Ci.galkoxyCi.galkoxy, Ci ⁇ alkanoyl, nitro, trifluoromethyl, cyano, SR 9 , SOR 9 , SO R 9 , SO 2 NR 10 R 1 1, CO 2 R 10 , CONR 10 R ⁇ , CO2NR 10 R n , CONR 10 (CH2)cC ⁇ 2R ⁇ , (CH2)cNR 10 R ⁇ , (CH 2 ) C CONR10R1 1, (CH 2 ) c NR 10 COR*l l, (CH 2 )cCO 2 C 1 -.6
- R 9 , R!0 and R * are independently hydrogen or C galkyl and c is 1 to 4;
- R2 is hydrogen, halogen, Cj.galkyl, C3_6cycloalkyl, C3_6cycloalkenyl, Ci. ⁇ lko y, C ⁇ _ galkanoyl, aryl, acyloxy, hydroxy, nitro, trifluoromethyl, cyano, CO2R 10 , CONR l 0 Rl !,
- R 10 and R 1 1 are as defined for R 1 ; a is 1, 2 or 3; or R a is a group of formula (ii)
- P-2 and P ⁇ are independently phenyl, bicyclic aryl, a 5- to 7- membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulphur, or a bicyclic heterocyclic group containing 1 to 3 heteroatoms selected from oxygen, nitrogen or sulphur providing that at least one of P-2 and P ⁇ is a bicyclic aryl or bicyclic heterocyclic group;
- A is a bond or oxygen, S(O) m where m is 0 to 2, carbonyl, or CH2 or NR4 where R ⁇ is hydrogen or C ⁇ _6alkyl;
- R! is as defined above for formula (i) or is a 5 to 7-membered heterocyclic ring, containing 1 to 3 heteroatoms selected from oxygen, nitrogen or sulphur, optionally substituted by C ⁇ _6alkyl, halogen or Cj.g alkanoyl;
- R-2 and R-3 are independently hydrogen, halogen, Cj.galkyl, C3_gcycloalkyl, C3_6cycloalkenyl, C ⁇ .galkoxy, Ci.galkanoyl, aryl, acyloxy, hydroxy, nitro, trifluoromethyl, cyano, CO2R 10 , CONR ⁇ R 1 1, NR ⁇ R* 1 where R 10 and R 1 1 are as defined for R 1 ; and a and b are independently 1, 2 or 3;
- L is a group of formula
- V oxygen or sulphur
- D is nitrogen, carbon or a CH group
- G is hydrogen or C galkyl, providing that D is nitrogen or a CH group, or G together with R°l forms a group W
- W is (CR ⁇ R ⁇ 7 )t where t is 2, 3 or 4 and R 1 ⁇ and R1? are independently hydrogen or C ⁇ .
- B is oxygen, S(O) p where p is 0, 1 or 2, NR ⁇ where R ⁇ is hydrogen or C ⁇ galkyl or B is
- CR CR where R 7 and R ⁇ are independently hydrogen or
- R c and R ⁇ are independently hydrogen or C ⁇ . ⁇ alkyl
- RY is a 5- to 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulphur, or RY is a group of formula - NR e R ⁇ in which
- R e and R-f are independently hydrogen, Cj.galkyl, or aralkyi;
- Rbl and R°2 are independently hydrogen, halogen, hydroxy, Cj.galkyl, trifluoromethyl, C ⁇ alkoxy or aryl, or R°l together with G forms a group W as defined above; and n is 1 to 4.
- C ⁇ alkyl groups whether alone or as part of another group may be straight chain or branched.
- acyloxy' is used herein to describe a group -OC(O)C ⁇ _6alkyl.
- 'aryl' is used herein to describe, unless otherwise stated, a group such as phenyl.
- 'aralkyi' is used herein to describe, unless otherwise stated, a group such as benzyl.
- the bicyclic aryl group represented by pi, P-2 and or p which may be partially saturated, is preferably naphthyl.
- bicyclic heterocyclic rings containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulphur include quinoline, isoquinoline, indole, benzofuran and benzothiophene rings.
- the heterocyclic groups can be linked to the remainder of the molecule via a carbon atom or, when present, a suitable nitrogen atom.
- Examples of 5 to 7 membered heterocyclic rings containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulphur represented by pi, P-2 and or p3, include thienyl, furyl, pyrrolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, isothiazolyl, isoxazolyl, thiadiazolyl, pyrimidyl and pyrazinyl, preferably pyridyl.
- R! is preferably a halogen atom for example, fluorine, chlorine or bromine, and R2 and/or R3 are each preferably hydrogen, halogen for example a chloro group or a C 1. galkyl group for example a methyl group.
- a and b are each preferably 1 or 2.
- A is preferably a bond or oxygen.
- group L, as defined above :- V is preferably oxygen.
- D is preferably nitrogen and G is preferably a hydrogen atom or together with R°l forms group W, preferably -(CH2)2 _ -
- R°l and R°2 are preferably hydrogen or a halogen atom for example chlorine or iodine, or a C ⁇ alkoxy group for example methoxy , or R°l together with G forms group W referred to above.
- R c and R ⁇ are preferably hydrogen.
- RY is preferably a dialkylamino(e.g. dimethylamino) group, n is preferably 2.
- the group B-(CR c R ⁇ ) n -Ry has a meta relationship with respect to the group R a L.
- the group R°2 has a para relationship with respect to the group R a L.
- Particularly preferred compounds according to the invention include :- N- [3 -(2-dimethylaminoethoxy)-4-iodophenyl]naphth- 1 -ylcarboxamide N- [3 -(2-dimethylaminoethoxy)-4-iodopheny 1] quinolin-4-y lcarboxamide or pharmaceutically acceptable salts thereof.
- Preferred salts of the compounds of formula (I) are pharmaceutically acceptable salts. These include acid addition salts such as hydrochlorides, hydrobromides, phosphates, acetates, fumarates, maleates, tartrates, citrates, oxalates, methanesulphonates and p-toluenesulphonates. Certain compounds of formula (I) are capable of existing in stereoisomeric forms.
- the invention encompasses all geometric and optical isomers of the compounds of formula (I) and the mixtures thereof including racemates.
- Compounds of the invention can be prepared using procedures known in the art.
- the present invention provides a process for the preparation of a compound of formula (I) or a pharmaceutically acceptable salt thereof which comprises coupling a compound of formula (II):
- R a , R°l, R ⁇ , R C ? RJ, Ry, B and n are as defined in formula (I) and L 1 and L 2 contain the appropriate functional groups which are capable of reacting together to form the L moiety; and optionally thereafter: • removing any protecting groups,
- L 1 is COL and L2 is NH 2
- L 1 is NH 2
- L 2 is COL a in which L a is an appropriate leaving group.
- one of L ⁇ and L 2 is an activated carboxylic acid derivative such as an acyl chloride or acid anhydride,and the other is an amine group.
- Activated compounds of formulae(II) and (III) can also be prepared by reaction of the corresponding carboxylic acid with a coupling agent such as dicyclohexylcarbodiimide,carbonyldiimidazole or diphenylphosphorylazide.
- L*-* or L 2 is a group COL a where L a is halo particularly chloro.
- Carboxylic acid groups can be protected as esters.
- Aldehyde or ketone groups can be protected as acetals, ketals, thioacetals or thioketals. Deprotection is achieved using standard conditions.
- 5HT ⁇ A/IB/ID receptor antagonists, and in particular the compounds of the present invention are expected to be of use in the treatment of CNS disorders such as mood disorders, including depression, seasonal affective disorder and dysthymia; anxiety disorders, including generalised anxiety, panic disorder, agoraphobia, social phobia, obsessive compulsive disorder and post-traumatic stress disorder; memory disorders, including dementia, amnestic disorders and age-associated memory impairment; disorders of eating behaviours, including anorexia nervosa and bulimia nervosa ;and sleep disorders.
- CNS disorders such as mood disorders, including depression, seasonal affective disorder and dysthymia; anxiety disorders, including generalised anxiety, panic disorder, agoraphobia, social phobia, obsessive
- CNS disorders include motor disorders such as Parkinson's disease, dementia in Parkinson's disease, neuroleptic-induced Parkinsonism and tardive dyskinesias, as well as other psychiatric disorders.
- SHTiA / TB/iE) receptor antagonists, and in particular compounds of the present invention may also be of use in the treatment of endocrine disorders such as hyperprolactinaemia, in the treatment of vasospasm (particularly in the cerebral vasculature) and hypertension, as well as disorders in the gastrointestinal tract where changes in motility and secretion are involved. They may also be of use in the treatment of sexual dysfunction and hypothermia.
- the present invention also provides a compound of general formula (I) or a physiologically acceptable salt or solvate thereof for use in the treatment of the aforementioned disorders.
- the invention provides a method of treating the aforementioned disorders which comprises administering an effective amount to a patient in need of such treatment of a compound of general formula (I) or a pharmaceutically acceptable salt or solvate thereof.
- the invention provides a compound of general formula (I) or a physiologically acceptable salt or solvate thereof for use in the treatment or prophylaxis of depression.
- the compounds according to the invention may advantageously be used in conjunction with one or more other therapeutic agents, for instance, different antidepressant agents.
- 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 infusible 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 colorants.
- 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 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.
- the composition may contain from 0.1% to 99% by weight, preferably from 10 to
- suitable unit doses may be 0.05 to 1000 mg, more suitably 1.0 to 200 mg, and such unit doses may be administered more than once a day, for example two or three a day. Such therapy may extend for a number of weeks or months.
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9707830.7A GB9707830D0 (en) | 1997-04-18 | 1997-04-18 | Novel compounds |
GB9707830.7 | 1997-04-18 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1998050343A2 true WO1998050343A2 (en) | 1998-11-12 |
WO1998050343A3 WO1998050343A3 (en) | 2001-04-12 |
Family
ID=10810957
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/002266 WO1998050343A2 (en) | 1997-04-18 | 1998-04-14 | (hetero)aryl carboxamide derivatives, process for their preparation and their use in the treatment of cns disorders |
Country Status (2)
Country | Link |
---|---|
GB (1) | GB9707830D0 (en) |
WO (1) | WO1998050343A2 (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000068184A1 (en) * | 1999-05-10 | 2000-11-16 | Warner-Lambert Company | Aromatic amides |
US7696223B2 (en) | 2006-04-04 | 2010-04-13 | Fibrogen, Inc. | Pyrrolo- and Thiazolo-pyridine compounds, and methods of use thereof |
US7928120B2 (en) | 2006-01-27 | 2011-04-19 | Fibrogen, Inc. | Cyanoisoquinoline compounds and methods of use thereof |
US8084614B2 (en) | 2007-04-06 | 2011-12-27 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
US8263588B2 (en) | 2007-04-06 | 2012-09-11 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
US8927591B2 (en) | 2008-11-14 | 2015-01-06 | Fibrogen, Inc. | Thiochromene derivatives as HIF hydroxylase inhibitors |
US9643928B2 (en) | 2013-01-24 | 2017-05-09 | Fibrogen, Inc. | Crystalline forms of {[1-cyano-5-(4-chlorophenoxy)-4-hydroxy-isoquinoline-3-carbonyl]-amino}-acetic acid |
US11325883B2 (en) | 2017-11-22 | 2022-05-10 | Temple University—Of the Commonwealth System of Higher Education | Functionalized N,N-dialkylamino phenyl ethers and their method of use |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995015954A1 (en) * | 1993-12-07 | 1995-06-15 | Smithkline Beecham Plc | Heterocyclic biphenylylamides useful as 5ht1d antagonists |
WO1995017398A1 (en) * | 1993-12-21 | 1995-06-29 | Smithkline Beecham Plc | Indole, indoline and quinoline derivatives with 5ht1d (anti-depressive) activity |
WO1995026328A1 (en) * | 1994-03-26 | 1995-10-05 | Smithkline Beecham Plc | Biphenyl derivatives as 5ht1d antagonists |
WO1996006079A1 (en) * | 1994-08-23 | 1996-02-29 | Smithkline Beecham Plc | Biphenylamide derivatives as 5ht1d antagonists |
-
1997
- 1997-04-18 GB GBGB9707830.7A patent/GB9707830D0/en active Pending
-
1998
- 1998-04-14 WO PCT/EP1998/002266 patent/WO1998050343A2/en active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995015954A1 (en) * | 1993-12-07 | 1995-06-15 | Smithkline Beecham Plc | Heterocyclic biphenylylamides useful as 5ht1d antagonists |
WO1995017398A1 (en) * | 1993-12-21 | 1995-06-29 | Smithkline Beecham Plc | Indole, indoline and quinoline derivatives with 5ht1d (anti-depressive) activity |
WO1995026328A1 (en) * | 1994-03-26 | 1995-10-05 | Smithkline Beecham Plc | Biphenyl derivatives as 5ht1d antagonists |
WO1996006079A1 (en) * | 1994-08-23 | 1996-02-29 | Smithkline Beecham Plc | Biphenylamide derivatives as 5ht1d antagonists |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000068184A1 (en) * | 1999-05-10 | 2000-11-16 | Warner-Lambert Company | Aromatic amides |
US6846953B1 (en) | 1999-05-10 | 2005-01-25 | Warner Lambert Company | Aromatic amides |
US9174976B2 (en) | 2006-01-27 | 2015-11-03 | Fibrogen, Inc. | Cyanoisoquinoline compounds and methods of use thereof |
US8759373B2 (en) | 2006-01-27 | 2014-06-24 | Fibrogen, Inc. | Cyanoisoquinoline compounds and methods of use thereof |
US7928120B2 (en) | 2006-01-27 | 2011-04-19 | Fibrogen, Inc. | Cyanoisoquinoline compounds and methods of use thereof |
US7696223B2 (en) | 2006-04-04 | 2010-04-13 | Fibrogen, Inc. | Pyrrolo- and Thiazolo-pyridine compounds, and methods of use thereof |
US10336769B2 (en) | 2007-04-06 | 2019-07-02 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
US8507536B2 (en) | 2007-04-06 | 2013-08-13 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
US8481738B2 (en) | 2007-04-06 | 2013-07-09 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
US8952161B2 (en) | 2007-04-06 | 2015-02-10 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
US8263588B2 (en) | 2007-04-06 | 2012-09-11 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
US9422310B2 (en) | 2007-04-06 | 2016-08-23 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
US8084614B2 (en) | 2007-04-06 | 2011-12-27 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
US10941159B2 (en) | 2007-04-06 | 2021-03-09 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
US11713324B2 (en) | 2007-04-06 | 2023-08-01 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
US8927591B2 (en) | 2008-11-14 | 2015-01-06 | Fibrogen, Inc. | Thiochromene derivatives as HIF hydroxylase inhibitors |
US9149476B2 (en) | 2008-11-14 | 2015-10-06 | Fibrogen, Inc. | Thiochromene derivatives as HIF hydroxylase inhibitors |
US9643928B2 (en) | 2013-01-24 | 2017-05-09 | Fibrogen, Inc. | Crystalline forms of {[1-cyano-5-(4-chlorophenoxy)-4-hydroxy-isoquinoline-3-carbonyl]-amino}-acetic acid |
US11325883B2 (en) | 2017-11-22 | 2022-05-10 | Temple University—Of the Commonwealth System of Higher Education | Functionalized N,N-dialkylamino phenyl ethers and their method of use |
Also Published As
Publication number | Publication date |
---|---|
GB9707830D0 (en) | 1997-06-04 |
WO1998050343A3 (en) | 2001-04-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5905080A (en) | Amide and urea derivatives as 5HT1D receptor antagonists | |
EP0736025B1 (en) | Dyhydrobenzofuranyl-biphenyl carboxamides having 5ht1d antagonistic activity | |
WO1998047868A1 (en) | Heterocycle-containing urea derivatives as 5ht1a, 5ht1b and 5ht1d receptor antagonists | |
JPH06107649A (en) | Benzanilide derivative | |
US5919932A (en) | Biphenylamide derivatives as 5HT1D antagonists | |
EP0712397B1 (en) | Amide derivatives as 5ht1d receptor antagonists | |
JPH06107637A (en) | Benzanilide derivative | |
US5696122A (en) | Indole and indoline derivatives as 5HT1D receptor antagonists | |
KR100295027B1 (en) | Aryl glycinamide derivative, preparation method and urination disorder therapeutics containing the derivative as active ingredient | |
EP0724580A1 (en) | Benzanilide derivatives as 5ht-1d receptor antagonists | |
WO1995006644A1 (en) | Amide derivatives as 5ht1d receptor antagonists | |
JP5852269B2 (en) | Novel morpholinyl derivatives useful as MOGAT-2 inhibitors | |
WO1995030675A1 (en) | Biphenylcarboxamides useful as 5-ht1d antagonists | |
WO2004080986A1 (en) | Phenyl sulfone derivatives and their use in the treatment of cns disorders | |
WO1998050343A2 (en) | (hetero)aryl carboxamide derivatives, process for their preparation and their use in the treatment of cns disorders | |
EP0777650B1 (en) | Biphenylamide derivatives as 5ht 1d antagonists | |
JP2009542707A (en) | Butyl and butynylbenzylamine compounds | |
EP0946551A2 (en) | N-piperazin-1-ylphenyl-benzamide derivatives | |
WO1997034900A1 (en) | Azaspiro derivatives | |
EP0752982B1 (en) | Biphenyl derivatives as 5ht1d antagonists | |
EP0877747A1 (en) | Azaspiro derivatives with 5ht 1b? activity | |
JP3041834B2 (en) | N-aminoalkyl-2-anthraquinone carboxamides; new ligands specific for dopamine receptor subtype | |
EP0889893A1 (en) | Azaspiroderivatives | |
EP0889892A1 (en) | Azaspiro derivatives | |
CA2238162A1 (en) | Tricyclic spiro compounds as 5ht1d receptor antagonists |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A2 Designated state(s): CA JP US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A2 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
NENP | Non-entry into the national phase in: |
Ref country code: JP Ref document number: 1998547662 Format of ref document f/p: F |
|
122 | Ep: pct application non-entry in european phase | ||
NENP | Non-entry into the national phase in: |
Ref country code: CA |
|
AK | Designated states |
Kind code of ref document: A3 Designated state(s): CA JP US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A3 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE |