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WO1984003281A1 - Derives anylides et benzamides d'azabicycloalkyle - Google Patents

Derives anylides et benzamides d'azabicycloalkyle Download PDF

Info

Publication number
WO1984003281A1
WO1984003281A1 PCT/GB1984/000047 GB8400047W WO8403281A1 WO 1984003281 A1 WO1984003281 A1 WO 1984003281A1 GB 8400047 W GB8400047 W GB 8400047W WO 8403281 A1 WO8403281 A1 WO 8403281A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
alkyl
hydrogen
compound
alkoxy
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.)
Ceased
Application number
PCT/GB1984/000047
Other languages
English (en)
Inventor
Christine Summers
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 GB838304648A external-priority patent/GB8304648D0/en
Priority claimed from GB838328550A external-priority patent/GB8328550D0/en
Application filed by Beecham Group PLC filed Critical Beecham Group PLC
Publication of WO1984003281A1 publication Critical patent/WO1984003281A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • E 1 is O, S or NR' wherein R'is hydrogen, methyl or acetyl
  • R 4 is of formula (II).
  • R 5 when -(CH 2 )tR 11 , are those wherein t is 1 and R 11 is unsubstituted phenyl or monosubsti tuted phenyl in particular mono-p-substituted phenyl.
  • preferred p-substitutents include methyl, trifluoromethyl, fluoro, chloro and bromo, especially fluoro.
  • Unsubstituted benzyl, p-fluorobenzyl, p-chlorobenzyl and p-methylbenzyl are especially preferred examples of R 5 .
  • Suitable examples of R 1 include hydrogen, methyl, ethyl, n- and iso-propyl.
  • R 1 is hydrogen or methyl.
  • R 2 and R 3 are independently hydrogen, chloro, amino or optionally substituted aminosulphonyl, as defined.
  • Particularly preferred compounds are those wherein R 2 5 is benzyl optionally substituted in the phenyl ring by one or two substituents selected from C 1-4 alkoxy, trifluoromethyl, halogen and C 1-4 alkyl.
  • variable groups are as hereinbefore defined under formula (XIV).
  • R 21 is hydrogen or C 1-4 alkanoyl
  • the invention also provides a process for the preparation of a compound of the formula (I), which process comprises reacting a compound of the formula (XIX):
  • the leaving group Q is a group that is readily displaceable by a nucleophile.
  • examples of such groups are hydroxy, halogen such as chloro and bromo, acyloxy such as C 1-4 alkanoyloxy, C 1-4 alkoxycarbonyloxy and activiated hydrocarbyloxy such as pentachlorophenoxy.
  • Another example of an acyloxy group Q is when Q is joined to E 1 to form -O-CO-N'-.
  • E-A moiety in compounds of the formula (XIX) is generally prepared by a cyclisation reaction.
  • E-A is of sub-formula (a) or (c) and E 1 is 0, the chroman/dihydrobenzofuran nucleus may be prepared according to the following scheme:
  • the compounds of the present invention are dopamine antagonists and may generally be used in the treatment of emesis. Depending on their balance between peripheral and central action on the nervous system, they may also be used in the treatment of disorders relating to impaired gastro-i ntestinal motility, such as retarded gastric emptying, dyspepsia, flatulence, oesophagal reflux and peptic ulcer and/or in the treatment of disorders of the central nervous system, such as psychosis. Certain of the compounds of formula have blood pressure lowering activity and may also be useful in the treatment of hypertension.
  • Parenteral suspensions are prepared in substantially the same manner except that the compound is suspended in the vehicle instead of being dissolved and sterilized by exposure to ethylene oxide before suspending in the sterile vehicle.
  • a surfactant or wetting agent is included in the composition to facilitate uniform distribution of the compound of the invention.
  • the invention further provides a method of treatment of disorders in mammals, such as humans, which comprises the administration of an effective amount of a compound of the formula (I) , or a pharmaceutically acceptable salt thereof, or an hydrate or N-oxide thereof, or a pharmaceutical composition, as hereinbefore defined to the sufferer.
  • the present invention also provides a pharmaceutical compositions comprising a compound of the formula (I) and an analgesic.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Composés de formule (I) ou un sel pharmaceutiquement acceptable et/ou un N-oxyde et/ou un produit de solvatation de ceux-ci dans laquelle soit X soit Y représente CO et l'autre NH; E représente O, S ou NR où R représente l'hydrogène, C1-6 alkyle ou un groupe de protection et A représente un C2-4 alkylène ou un C2-4 alkénylène ou E et A forment ensemble avec le phényle auquel ils sont rattachés un noyau de quinoline; R4 est un groupe (II), (III), (IV) dans lesquels p et q valent indépendamment entre 0 et 2; Z représente O ou S; n vaut 0 ou 1; ces composés ont une activité antagoniste de la dopamine; leur procédé de préparation et leur utilisation en tant que produit pharmaceutique.
PCT/GB1984/000047 1983-02-19 1984-02-17 Derives anylides et benzamides d'azabicycloalkyle Ceased WO1984003281A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB838304648A GB8304648D0 (en) 1983-02-19 1983-02-19 Compounds
GB838328550A GB8328550D0 (en) 1983-10-26 1983-10-26 Compounds

Publications (1)

Publication Number Publication Date
WO1984003281A1 true WO1984003281A1 (fr) 1984-08-30

Family

ID=26285285

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1984/000047 Ceased WO1984003281A1 (fr) 1983-02-19 1984-02-17 Derives anylides et benzamides d'azabicycloalkyle

Country Status (2)

Country Link
EP (1) EP0135545A1 (fr)
WO (1) WO1984003281A1 (fr)

Cited By (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0147044A3 (en) * 1983-12-22 1985-11-21 Adria Laboratories Inc. Benzofurancarboxamides, process for their preparation and pharmaceutical preparations containing them
FR2575750A1 (fr) * 1985-01-07 1986-07-11 Sandoz Sa Derives de la piperidine et de la pyrrolidine, leur preparation et leur utilisation comme medicaments
EP0190860A3 (fr) * 1985-01-30 1987-06-03 Smithkline Beecham Corporation 6-Chloro-3-méthyl-1H-2,3,4,5-tétrahydro-3-benzazépine-N-oxyde et composition médicale le contenant
EP0230718A1 (fr) * 1985-11-02 1987-08-05 Beecham Group Plc Benzamides et benzoates substitués
EP0234872A1 (fr) * 1986-02-28 1987-09-02 Erbamont Inc. Carboxamides utiles comme agents antiémétiques ou antipsychotiques
WO1988001866A1 (fr) * 1986-09-09 1988-03-24 Adria Laboratories, Inc. Procede permettant de soulager les vomissements provoques par les substances utilisees en chimiotherapie et agents anti-emetiques utilises dans ces substances
EP0231139A3 (en) * 1986-01-30 1988-04-27 Laboratoires Delagrange Dihydrobenzofurane and chromane carboxamide derivatives, processes for their preparation and their use as neuroleptics
US4803199A (en) * 1982-06-29 1989-02-07 Peter Donatsch Pharmaceutically useful heterocyclic and carbocyclic acid esters and amides of alkylene bridged piperidines
US4851407A (en) * 1985-03-14 1989-07-25 Beecham Group, P.L.C. Novel treatment
US4910193A (en) * 1985-12-16 1990-03-20 Sandoz Ltd. Treatment of gastrointestinal disorders
US4921982A (en) * 1988-07-21 1990-05-01 Eli Lilly And Company 5-halo-2,3-dihydro-2,2-dimethylbenzofuran-7-carboxylic acids useful as intermediates for 5-HT3 antagonists
WO1990006113A1 (fr) * 1988-11-29 1990-06-14 Rorer International (Overseas) Inc. Carboxamides d'indole quinoline et benzazepine substitues satures et non satures et leur utilisation en tant qu'agents pharmacologiques
EP0307172A3 (fr) * 1987-09-08 1991-01-23 Eli Lilly And Company 5-HT3-antagonistes spécifiques
EP0416521A1 (fr) * 1989-09-05 1991-03-13 G.D. Searle & Co. N-Benzyltropaneamides
US5001133A (en) * 1983-12-23 1991-03-19 Sandoz Ltd. Benzoic acid derivatives
WO1991005783A1 (fr) * 1989-10-14 1991-05-02 John Wyeth & Brother Limited Composes heterocycliques
EP0339950A3 (fr) * 1988-04-27 1991-05-15 Rhone-Poulenc Rorer International (Holdings) Inc. Dibenzofurancarboxamides, leur utilisation comme agents pharmaceutiques, composition les contenant et procédé de préparation
EP0445862A2 (fr) 1990-03-06 1991-09-11 Janssen Pharmaceutica N.V. Dérivés de la N-(4-pipéridinyl-)-dihydrobenzofurane- ou de ca dihydro-2H-benzopyrannecarboxamide
US5049556A (en) * 1988-03-23 1991-09-17 Beecham Group P.L.C. Certain N-azabicyclo-2,3-dihydro-indole-1-carboxamides having anti-emetic properties, further found useful in treating headaches, neuralgia and anxiety
US5063230A (en) * 1988-11-29 1991-11-05 Rhone-Poulenc Rorer Pharmaceuticals Inc. Substituted saturated and unsaturated indole quinoline and benzazepine carboxamides and their use as pharmacological agents
EP0493031A1 (fr) * 1990-12-27 1992-07-01 PHARMACIA S.p.A. Carboxamides de dihydrobenzofuranne et procédé pour leur préparation
WO1992012147A1 (fr) * 1990-12-27 1992-07-23 Farmitalia Carlo Erba S.R.L. Procede de preparation de derives de benzofuranne substitues
US5142069A (en) * 1991-03-07 1992-08-25 Eli Lilly And Company Process of preparing 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acids
US5175173A (en) * 1983-12-22 1992-12-29 Sun Jung Hui Carboxamides useful as antiemetic or antipsychotic agents
US5177244A (en) * 1991-03-07 1993-01-05 Eli Lilly And Company Process and intermediates to 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acids
EP0189002B1 (fr) * 1984-12-20 1993-03-03 Sandoz Ag Traitement de maladies gastro-intestinales utilisant des 5-HT3 antagonistes
EP0247266B1 (fr) * 1986-01-07 1993-03-10 Beecham Group Plc Dérivés d'indole ayant une chaîne latérale azabicyclique, procédé pour leur préparation, produits intermédiaires et compositions pharmaceutiques
US5225419A (en) * 1989-10-14 1993-07-06 John Wyeth & Brother, Limited Certain 1,8-ethano or propano-1,4-dihydro-4-oxo-quinoline-3-carboxamides and derivatives thereof
US5364863A (en) * 1987-09-08 1994-11-15 Eli Lilly And Company Specific 5-HT3 antagonists
US5446147A (en) * 1992-04-03 1995-08-29 Trustees Of The University Of Pennsylvania Fluorinated and iodinated dopamine agents
CN1040756C (zh) * 1989-10-14 1998-11-18 约翰韦恩兄弟有限公司 杂环化合物的制备方法
US8629274B2 (en) 2011-12-21 2014-01-14 Novira Therapeutics, Inc. Hepatitis B antiviral agents
US8993771B2 (en) 2013-03-12 2015-03-31 Novira Therapeutics, Inc. Hepatitis B antiviral agents
US9169212B2 (en) 2014-01-16 2015-10-27 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
US9181288B2 (en) 2014-01-16 2015-11-10 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
US9400280B2 (en) 2014-03-27 2016-07-26 Novira Therapeutics, Inc. Piperidine derivatives and methods of treating hepatitis B infections
US9884831B2 (en) 2015-03-19 2018-02-06 Novira Therapeutics, Inc. Azocane and azonane derivatives and methods of treating hepatitis B infections
US9884818B2 (en) 2013-05-17 2018-02-06 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US9895349B2 (en) 2013-04-03 2018-02-20 Janssen Sciences Ireland Us N-phenyl-carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10071961B2 (en) 2013-10-23 2018-09-11 Janssen Sciences Ireland Uc Carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10077239B2 (en) 2015-09-29 2018-09-18 Novira Therapeutics, Inc. Crystalline forms of a hepatitis B antiviral agent
US10125094B2 (en) 2013-02-28 2018-11-13 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US10213420B2 (en) 2014-02-05 2019-02-26 Novira Therapeutics, Inc. Combination therapy for treatment of HBV infections
US10392349B2 (en) 2014-01-16 2019-08-27 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
US10441589B2 (en) 2016-04-15 2019-10-15 Novira Therapeutics, Inc. Combinations and methods comprising a capsid assembly inhibitor
US10450270B2 (en) 2013-07-25 2019-10-22 Janssen Sciences Ireland Uc Glyoxamide substituted pyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10676429B2 (en) 2012-08-28 2020-06-09 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US10875876B2 (en) 2015-07-02 2020-12-29 Janssen Sciences Ireland Uc Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10973801B2 (en) 2018-03-14 2021-04-13 Janssen Sciences Ireland Unlimited Company Capsid assembly modulator dosing regimen
US11078193B2 (en) 2014-02-06 2021-08-03 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US11096931B2 (en) 2019-02-22 2021-08-24 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases
US11491148B2 (en) 2019-05-06 2022-11-08 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0068700A1 (fr) * 1981-06-29 1983-01-05 Beecham Group Plc Azabicycloalkylbenzamides, leur procédé de préparation et les compositions pharmaceutiques les contenant
EP0095262A1 (fr) * 1982-05-11 1983-11-30 Beecham Group Plc Dérivés de l'azabicycloalkane, leur préparation et médicaments les contenant
WO1984000166A1 (fr) * 1982-06-29 1984-01-19 Sandoz Ag Derives d'ester piperidyl d'acide benzoique et procede de production et d'utilisation de ces composes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0068700A1 (fr) * 1981-06-29 1983-01-05 Beecham Group Plc Azabicycloalkylbenzamides, leur procédé de préparation et les compositions pharmaceutiques les contenant
EP0095262A1 (fr) * 1982-05-11 1983-11-30 Beecham Group Plc Dérivés de l'azabicycloalkane, leur préparation et médicaments les contenant
WO1984000166A1 (fr) * 1982-06-29 1984-01-19 Sandoz Ag Derives d'ester piperidyl d'acide benzoique et procede de production et d'utilisation de ces composes

Cited By (85)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4910207A (en) * 1982-06-29 1990-03-20 Peter Donatsch Method of treating psychosis with N-quinuclidinyl-benzamides
US5017582A (en) * 1982-06-29 1991-05-21 Sandoz Ltd. Method of inducing a serotonin M receptor antagonist effect with N-quinuclidinyl-benzamides
US4803199A (en) * 1982-06-29 1989-02-07 Peter Donatsch Pharmaceutically useful heterocyclic and carbocyclic acid esters and amides of alkylene bridged piperidines
EP0147044A3 (en) * 1983-12-22 1985-11-21 Adria Laboratories Inc. Benzofurancarboxamides, process for their preparation and pharmaceutical preparations containing them
US5175173A (en) * 1983-12-22 1992-12-29 Sun Jung Hui Carboxamides useful as antiemetic or antipsychotic agents
US5001133A (en) * 1983-12-23 1991-03-19 Sandoz Ltd. Benzoic acid derivatives
EP0189002B1 (fr) * 1984-12-20 1993-03-03 Sandoz Ag Traitement de maladies gastro-intestinales utilisant des 5-HT3 antagonistes
FR2575750A1 (fr) * 1985-01-07 1986-07-11 Sandoz Sa Derives de la piperidine et de la pyrrolidine, leur preparation et leur utilisation comme medicaments
EP0190860A3 (fr) * 1985-01-30 1987-06-03 Smithkline Beecham Corporation 6-Chloro-3-méthyl-1H-2,3,4,5-tétrahydro-3-benzazépine-N-oxyde et composition médicale le contenant
US4851407A (en) * 1985-03-14 1989-07-25 Beecham Group, P.L.C. Novel treatment
EP0230718A1 (fr) * 1985-11-02 1987-08-05 Beecham Group Plc Benzamides et benzoates substitués
US4853394A (en) * 1985-11-02 1989-08-01 Beecham Group P.L.C. N-('-B-hydroxyethylpiperid-4-yl esters and amides
US4910193A (en) * 1985-12-16 1990-03-20 Sandoz Ltd. Treatment of gastrointestinal disorders
EP0247266B1 (fr) * 1986-01-07 1993-03-10 Beecham Group Plc Dérivés d'indole ayant une chaîne latérale azabicyclique, procédé pour leur préparation, produits intermédiaires et compositions pharmaceutiques
AU593605B2 (en) * 1986-01-30 1990-02-15 Laboratoires Delagrange New dihydrobenzofuran- and chroman-carboxamide derivatives, processes for the preparation thereof and use thereof as neuroleptics
EP0231139A3 (en) * 1986-01-30 1988-04-27 Laboratoires Delagrange Dihydrobenzofurane and chromane carboxamide derivatives, processes for their preparation and their use as neuroleptics
US4888353A (en) * 1986-02-28 1989-12-19 Erbamont, Inc. Carboxamides useful as antiemetic or antipsychotic agents
EP0234872A1 (fr) * 1986-02-28 1987-09-02 Erbamont Inc. Carboxamides utiles comme agents antiémétiques ou antipsychotiques
US4772459A (en) * 1986-09-09 1988-09-20 Erbamont, Inc. Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein
WO1988001866A1 (fr) * 1986-09-09 1988-03-24 Adria Laboratories, Inc. Procede permettant de soulager les vomissements provoques par les substances utilisees en chimiotherapie et agents anti-emetiques utilises dans ces substances
US5364863A (en) * 1987-09-08 1994-11-15 Eli Lilly And Company Specific 5-HT3 antagonists
AU609185B2 (en) * 1987-09-08 1991-04-26 Eli Lilly And Company Improvements in or relating to specific 5-ht3 antagonists
AU638790B2 (en) * 1987-09-08 1993-07-08 Eli Lilly And Company Intermediates in the preparation of novel bicyclic esters and amides useful as specific 5-ht3 antagonists
EP0307172A3 (fr) * 1987-09-08 1991-01-23 Eli Lilly And Company 5-HT3-antagonistes spécifiques
US5563148A (en) * 1987-09-08 1996-10-08 Eli Lilly And Company Specific 5-HT3 antagonists
US5442078A (en) * 1987-09-08 1995-08-15 Eli Lilly And Company Intermediates for specific 5-HT3 antagonists
US5049556A (en) * 1988-03-23 1991-09-17 Beecham Group P.L.C. Certain N-azabicyclo-2,3-dihydro-indole-1-carboxamides having anti-emetic properties, further found useful in treating headaches, neuralgia and anxiety
EP0339950A3 (fr) * 1988-04-27 1991-05-15 Rhone-Poulenc Rorer International (Holdings) Inc. Dibenzofurancarboxamides, leur utilisation comme agents pharmaceutiques, composition les contenant et procédé de préparation
US4921982A (en) * 1988-07-21 1990-05-01 Eli Lilly And Company 5-halo-2,3-dihydro-2,2-dimethylbenzofuran-7-carboxylic acids useful as intermediates for 5-HT3 antagonists
WO1990006113A1 (fr) * 1988-11-29 1990-06-14 Rorer International (Overseas) Inc. Carboxamides d'indole quinoline et benzazepine substitues satures et non satures et leur utilisation en tant qu'agents pharmacologiques
US5063230A (en) * 1988-11-29 1991-11-05 Rhone-Poulenc Rorer Pharmaceuticals Inc. Substituted saturated and unsaturated indole quinoline and benzazepine carboxamides and their use as pharmacological agents
EP0416521A1 (fr) * 1989-09-05 1991-03-13 G.D. Searle & Co. N-Benzyltropaneamides
CN1040756C (zh) * 1989-10-14 1998-11-18 约翰韦恩兄弟有限公司 杂环化合物的制备方法
US5225419A (en) * 1989-10-14 1993-07-06 John Wyeth & Brother, Limited Certain 1,8-ethano or propano-1,4-dihydro-4-oxo-quinoline-3-carboxamides and derivatives thereof
WO1991005783A1 (fr) * 1989-10-14 1991-05-02 John Wyeth & Brother Limited Composes heterocycliques
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