CA2755954C - Quaternary quinuclidine derivatives and their use as muscarinic receptor antagonists - Google Patents

Quaternary quinuclidine derivatives and their use as muscarinic receptor antagonists Download PDF

Info

Publication number
CA2755954C
CA2755954C CA2755954A CA2755954A CA2755954C CA 2755954 C CA2755954 C CA 2755954C CA 2755954 A CA2755954 A CA 2755954A CA 2755954 A CA2755954 A CA 2755954A CA 2755954 C CA2755954 C CA 2755954C
Authority
CA
Canada
Prior art keywords
methyl
azoniabicyclo
hydroxy
diphenyl
octane bromide
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.)
Expired - Lifetime
Application number
CA2755954A
Other languages
English (en)
French (fr)
Other versions
CA2755954A1 (en
Inventor
Dramane Ibrahim Laine
Michael R. Palovich
Brent W. Mccleland
Christopher E. Neipp
Sonia M. Thomas
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.)
Glaxo Group Ltd
Original Assignee
Glaxo Group 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=35242158&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2755954(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd
Publication of CA2755954A1 publication Critical patent/CA2755954A1/en
Application granted granted Critical
Publication of CA2755954C publication Critical patent/CA2755954C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/452—Piperidinium derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/02—Nasal agents, e.g. decongestants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Otolaryngology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
CA2755954A 2004-04-27 2005-04-27 Quaternary quinuclidine derivatives and their use as muscarinic receptor antagonists Expired - Lifetime CA2755954C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US56562304P 2004-04-27 2004-04-27
US60/565,623 2004-04-27
CA2564742A CA2564742C (en) 2004-04-27 2005-04-27 Quaternary quinuclidine derivatives and their use as muscarinic receptor antagonists

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2564742A Division CA2564742C (en) 2004-04-27 2005-04-27 Quaternary quinuclidine derivatives and their use as muscarinic receptor antagonists

Publications (2)

Publication Number Publication Date
CA2755954A1 CA2755954A1 (en) 2005-11-10
CA2755954C true CA2755954C (en) 2014-02-18

Family

ID=35242158

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2755954A Expired - Lifetime CA2755954C (en) 2004-04-27 2005-04-27 Quaternary quinuclidine derivatives and their use as muscarinic receptor antagonists
CA2564742A Expired - Lifetime CA2564742C (en) 2004-04-27 2005-04-27 Quaternary quinuclidine derivatives and their use as muscarinic receptor antagonists

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2564742A Expired - Lifetime CA2564742C (en) 2004-04-27 2005-04-27 Quaternary quinuclidine derivatives and their use as muscarinic receptor antagonists

Country Status (38)

Country Link
US (9) US7498440B2 (enExample)
EP (3) EP1740177B1 (enExample)
JP (2) JP5014121B2 (enExample)
KR (2) KR101037026B1 (enExample)
CN (2) CN1976701A (enExample)
AP (1) AP2213A (enExample)
AR (1) AR050902A1 (enExample)
AU (1) AU2005237576B2 (enExample)
BE (1) BE2014C063I2 (enExample)
BR (1) BRPI0510170B8 (enExample)
CA (2) CA2755954C (enExample)
CY (3) CY1113196T1 (enExample)
DK (2) DK2570128T3 (enExample)
EA (2) EA021994B1 (enExample)
EC (1) ECSP066940A (enExample)
ES (2) ES2600405T3 (enExample)
FR (1) FR14C0075I2 (enExample)
HR (2) HRP20120832T1 (enExample)
HU (2) HUE031304T2 (enExample)
IL (1) IL178152A (enExample)
LT (1) LT2570128T (enExample)
LU (1) LU92565I2 (enExample)
MA (1) MA28631B1 (enExample)
MX (1) MXPA06012405A (enExample)
MY (1) MY144753A (enExample)
NL (1) NL300694I1 (enExample)
NO (3) NO338959B1 (enExample)
NZ (1) NZ549997A (enExample)
PE (1) PE20060259A1 (enExample)
PL (2) PL2570128T3 (enExample)
PT (2) PT2570128T (enExample)
SG (1) SG186597A1 (enExample)
SI (2) SI2570128T1 (enExample)
TW (1) TWI363759B (enExample)
UA (1) UA95768C2 (enExample)
UY (1) UY28871A1 (enExample)
WO (1) WO2005104745A2 (enExample)
ZA (1) ZA200608565B (enExample)

Families Citing this family (78)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200519108A (en) * 2003-07-17 2005-06-16 Glaxo Group Ltd Muscarinic acetylcholine receptor antagonists
MXPA06004242A (es) * 2003-10-17 2006-06-28 Glaxo Group Ltd Antagonistas del receptor muscarinico de la acetilcolina.
TW200524577A (en) * 2003-11-04 2005-08-01 Glaxo Group Ltd Muscarinic acetylcholine receptor antagonists
WO2005087236A1 (en) * 2004-03-11 2005-09-22 Glaxo Group Limited Novel m3 muscarinic acetylcholine receptor antagonists
WO2005095407A1 (en) * 2004-03-17 2005-10-13 Glaxo Group Limited M3 muscarinic acetylcholine receptor antagonists
WO2005094251A2 (en) * 2004-03-17 2005-10-13 Glaxo Group Limited M3muscarinic acetylcholine receptor antagonists
US20080194619A1 (en) * 2004-04-05 2008-08-14 Laurent Lecanu Anti-Hiv Quinuclidine Compounds
AR050902A1 (es) 2004-04-27 2006-12-06 Glaxo Group Ltd Compuesto de quinuclidina, composicion farmaceutica que lo comprende y su usopara preparar dicha composicion
EP1747219A4 (en) * 2004-05-13 2010-05-26 Glaxo Group Ltd Antagonists of muscarinic acetylcholine receptor
GB0424284D0 (en) 2004-11-02 2004-12-01 Novartis Ag Organic compounds
JP2008520579A (ja) * 2004-11-15 2008-06-19 グラクソ グループ リミテッド 新規m3ムスカリン性アセチルコリン受容体アンタゴニスト
EP1937267A4 (en) * 2005-08-02 2009-08-26 Glaxo Group Ltd M3-MUSCARIN ACETYLCHOLIN RECEPTOR ANTAGONISTS
US7767691B2 (en) * 2005-08-18 2010-08-03 Glaxo Group Limited Muscarinic acetylcholine receptor antagonists containing an azoniabiocyclo[2.2.1] heptane ring system
EA200801997A1 (ru) 2006-04-20 2009-04-28 Глаксо Груп Лимитед Новые соединения
GB0611587D0 (en) 2006-06-12 2006-07-19 Glaxo Group Ltd Novel compounds
NZ574533A (en) 2006-08-01 2011-05-27 Glaxo Group Ltd Pyrazolo[3,4-b]pyridine compounds, and their use as pde4 inhibitors
AR065804A1 (es) 2007-03-23 2009-07-01 Smithkline Beecham Corp Compuesto de indol carboxamida, composicion farmaceutica que lo comprende y uso de dicho compuesto para preparar un medicamento
CL2009000249A1 (es) 2008-02-06 2009-09-11 Glaxo Group Ltd Compuestos derivados de pirazolo[3,4-b] piridin-butanodiamida; composicion farmaceutica; y su uso en el tratamiento del asma, enfermedad pulmonar obstructiva cronica, rinitis, dermatitis atopica, psoriasis.
UY31637A1 (es) 2008-02-06 2009-08-03 Farmacoforos duales-antagonistas muscarinicos de pde4
AR070564A1 (es) 2008-02-06 2010-04-21 Glaxo Group Ltd Derivados de 1h-pirazolo[3,4-b]piridin-5-ilo,inhibidores de fosfodiesterasas pde4 y antagonistas de receptores muscarinicos de acetilcolina(machr), utiles en el tratamiento y/o profilaxis de enfermedades respiratorias y alergicas,y composiciones farmaceuticas que los comprenden
EP2280946B1 (en) 2008-06-05 2016-02-10 Glaxo Group Limited 4-carboxamide indazole derivatives useful as inhibitors of p13-kinases
WO2009147190A1 (en) 2008-06-05 2009-12-10 Glaxo Group Limited Novel compounds
WO2010094643A1 (en) 2009-02-17 2010-08-26 Glaxo Group Limited Quinoline derivatives and their uses for rhinitis and urticaria
ES2739352T3 (es) 2009-02-26 2020-01-30 Glaxo Group Ltd Formulaciones farmacéuticas que comprenden 4-{(1R)-2-[(6-{2-[(2,6-diclorobencil)oxi]etoxi}hexil)amino]-1-hidroxietil}-2-(hidroximetil)fenol
US8524751B2 (en) 2009-03-09 2013-09-03 GlaxoSmithKline Intellecutual Property Development 4-oxadiazol-2-YL-indazoles as inhibitors of P13 kinases
US8354539B2 (en) 2009-03-10 2013-01-15 Glaxo Group Limited Indole derivatives as IKK2 inhibitors
JP2012520845A (ja) 2009-03-17 2012-09-10 グラクソ グループ リミテッド Itk阻害剤として使用されるピリミジン誘導体
RS53830B1 (sr) 2009-04-30 2015-06-30 Glaxo Group Limited Indazoli supstituisani oksazolom kao inhibitori pi3-kinaze
WO2011029896A1 (en) 2009-09-11 2011-03-17 Glaxo Group Limited Methods of preparation of muscarinic acetylcholine receptor antagonists
GB0921075D0 (en) 2009-12-01 2010-01-13 Glaxo Group Ltd Novel combination of the therapeutic agents
WO2011067365A1 (en) 2009-12-03 2011-06-09 Glaxo Group Limited Benzpyrazole derivatives as inhibitors of p13 kinases
WO2011067364A1 (en) 2009-12-03 2011-06-09 Glaxo Group Limited Novel compounds
EP2507231A1 (en) 2009-12-03 2012-10-10 Glaxo Group Limited Indazole derivatives as pi 3 - kinase inhibitors
ES2655083T3 (es) * 2010-01-28 2018-02-16 Theron Pharmaceuticals, Inc. Derivados de 7-azoniabiciclo [2.2.1]heptano, métodos de producción, y usos farmacéuticos de estos
WO2011110575A1 (en) 2010-03-11 2011-09-15 Glaxo Group Limited Derivatives of 2-[2-(benzo- or pyrido-) thiazolylamino]-6-aminopyridine, useful in the treatment of respiratoric, allergic or inflammatory diseases
CA2803418A1 (en) * 2010-06-22 2011-12-29 Chiesi Farmaceutici S.P.A. Dry powder formulation comprising an antimuscarinic drug
HRP20151017T1 (hr) 2010-09-08 2015-10-23 Glaxosmithkline Intellectual Property Development Limited Polimorfi i soli n-[5-[4-(5-{[(2r,6s)-2,6-dimetil-4-morfolinil]metil}-1,3-oksazol-2-il)-1h-indazol-6-il]-2-(metiloksi)-3-piridinil]metansulfonamida
WO2012035055A1 (en) 2010-09-17 2012-03-22 Glaxo Group Limited Novel compounds
GB201018124D0 (en) 2010-10-27 2010-12-08 Glaxo Group Ltd Polymorphs and salts
AU2012266541A1 (en) * 2011-06-08 2014-01-09 Glaxo Group Limited Combination comprising umeclidinium and a corticosteroid
WO2012168160A1 (en) 2011-06-08 2012-12-13 Glaxo Group Limited Dry powder inhaler compositions comprising umeclidinium
KR20140147891A (ko) 2012-04-13 2014-12-30 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 응집체 입자
RU2502743C1 (ru) * 2012-08-03 2013-12-27 Федеральное государственное бюджетное учреждение "Российский кардиологический научно-производственный комплекс" Министерства здравоохранения и социального развития РФ (ФГБУ "РКНПК" Минздравсоцразвития России) Синтетический антиген, обладающий способностью связывать аутоантитела к мускариновому м2-рецептору
JP6389174B2 (ja) * 2012-08-15 2018-09-12 グラクソ グループ リミテッドGlaxo Group Limited 化学的方法
GB201222679D0 (en) * 2012-12-17 2013-01-30 Glaxo Group Ltd Pharmaceutical combination products
RU2641285C2 (ru) * 2013-07-13 2018-01-17 Бэйцзин Фсвэлкам Текнолоджи Девелопмент Ко., Лтд Соединения хинина, способ их получения и их медицинское применение
HK1225317A1 (zh) 2013-07-30 2017-09-08 Glaxosmithkline Intellectual Property Development Limited 用於治疗过度出汗的局部组合物及其使用方法
EP3057588A1 (en) 2013-10-17 2016-08-24 GlaxoSmithKline Intellectual Property Development Limited Pi3k inhibitor for treatment of respiratory disease
KR20160062179A (ko) 2013-10-17 2016-06-01 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 호흡기 질병의 치료를 위한 pi3k 억제제
WO2015173701A2 (en) 2014-05-12 2015-11-19 Glaxosmithkline Intellectual Property (No. 2) Limited Pharmaceutical compositions for treating infectious diseases
US10987363B2 (en) 2014-05-28 2021-04-27 Glaxosmithkline Intellectual Property Development Limited Fluticasone furoate in the treatment of COPD
EP3215489B1 (en) 2014-11-03 2019-07-24 OLON S.p.A. Method for the preparation of 1-(2-halogen-ethyl)-4 piperidine-carboxylic acid ethyl esters
KR101613245B1 (ko) 2015-04-27 2016-04-18 주식회사 대웅제약 신규의 4-메톡시 피롤 유도체 또는 이의 염 및 이를 포함하는 약학 조성물
CN105461710A (zh) * 2015-10-23 2016-04-06 安徽德信佳生物医药有限公司 一种芜地溴铵的制备方法
MX384539B (es) * 2016-01-08 2025-03-14 Theron Pharmaceuticals Inc Composiciones de inhalador de polvo seco de derivados de 7-azoniabiciclo[2.2.1]heptano
GB201602527D0 (en) 2016-02-12 2016-03-30 Glaxosmithkline Ip Dev Ltd Chemical compounds
CN107200734B (zh) * 2016-03-18 2019-12-24 益方生物科技(上海)有限公司 奎宁环衍生物及其制备方法和用途
EP3248970A1 (en) 2016-05-27 2017-11-29 Zentiva K.S. Forms of umeclidinium bromide
EP3497100A1 (en) 2016-08-08 2019-06-19 GlaxoSmithKline Intellectual Property Development Limited Chemical compounds
PT109740B (pt) * 2016-11-14 2020-07-30 Hovione Farmaciencia Sa Processo para a preparação de brometo de umeclidínio
WO2018163212A1 (en) * 2017-03-08 2018-09-13 Gbr Laboratories Pvt. Ltd A process for the preparation of umeclidinium bromide and intermediates thereof
GB201706102D0 (en) 2017-04-18 2017-05-31 Glaxosmithkline Ip Dev Ltd Chemical compounds
IT201700058796A1 (it) 2017-05-30 2018-11-30 Olon Spa Procedimento per la preparazione di un nuovo intermedio di sintesi dell’umeclidinio.
GB201712081D0 (en) 2017-07-27 2017-09-13 Glaxosmithkline Ip Dev Ltd Chemical compounds
WO2019086463A1 (en) 2017-10-30 2019-05-09 Baxalta GmbH Environmentally compatible detergents for inactivation of lipid-enveloped viruses
CN108558860B (zh) * 2018-06-04 2020-12-25 成都伊诺达博医药科技有限公司 一种合成芜地溴铵的方法
US11484531B2 (en) 2018-08-30 2022-11-01 Theravance Biopharma R&D Ip, Llc Methods for treating chronic obstructive pulmonary disease
PT115583B (pt) 2019-06-17 2022-05-02 Hovione Farm S A Processo contínuo para a preparação de medicamentos anticolinérgicos
CN113387923A (zh) * 2020-03-13 2021-09-14 诺华股份有限公司 硫辛酸胆碱酯盐的药物组合物及使用其的治疗方法
CA3173172A1 (en) 2020-03-26 2021-09-30 Christopher D. Kane Cathepsin inhibitors for preventing or treating viral infections
CN111484445B (zh) * 2020-04-21 2021-05-18 广东莱佛士制药技术有限公司 分离纯化高纯度乌美溴铵的中间体的方法
US12358908B2 (en) 2020-04-26 2025-07-15 Beijing Showby Pharmaceutical Co., Ltd. Crystals, preparation method and application of a muscarinic receptor antagonist
AU2021341508A1 (en) 2020-09-10 2023-05-25 Precirix N.V. Antibody fragment against fap
CN112479983B (zh) * 2020-11-25 2022-07-12 江苏豪森药业集团有限公司 乌美溴铵中间体及其制备方法
PT117440B (pt) 2021-09-03 2024-04-26 Hovione Farm S A Processo para a preparação de aminas cíclicas cloroaquilo substituídas
WO2023203135A1 (en) 2022-04-22 2023-10-26 Precirix N.V. Improved radiolabelled antibody
AU2023264245A1 (en) 2022-05-02 2024-12-19 Precirix N.V. Pre-targeting
WO2024251812A1 (en) 2023-06-07 2024-12-12 Pharmazell Gmbh A process for the preparation of umeclidinium bromide intermediate

Family Cites Families (63)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2800481A (en) * 1955-07-01 1957-07-23 Smith Kline French Lab Tertiary alcohol derivatives of 8-alkylnortropanes and the acid and quaternary ammonium salts thereof
US2800478A (en) * 1955-07-01 1957-07-23 Smith Kline French Lab 3-substituted-8-alkylnortropanes and the acid and quaternary ammonium salts thereof
AT298118B (de) * 1967-06-08 1972-04-25 Siemens Ag Verfahren zur Umsetzung von Spannungen in digitale Werte und Vorrichtung zur Durchführung des Verfahrens
GB1242211A (en) 1967-08-08 1971-08-11 Fisons Pharmaceuticals Ltd Pharmaceutical composition
GB1230087A (enExample) 1967-08-17 1971-04-28
GB1381872A (en) 1971-06-22 1975-01-29 Fisons Ltd Pharmaceutical compositions for inhalation
CY1308A (en) 1979-12-06 1985-12-06 Glaxo Group Ltd Device for dispensing medicaments
EP0069715B1 (en) 1981-07-08 1986-11-05 Aktiebolaget Draco Powder inhalator
DK172541B1 (da) 1982-10-08 1998-12-07 Glaxo Group Ltd Apparat til administrering af medikamenter til patienter og en medikamentpakning til brug i apparatet
GB2169265B (en) 1982-10-08 1987-08-12 Glaxo Group Ltd Pack for medicament
AU591152B2 (en) 1985-07-30 1989-11-30 Glaxo Group Limited Devices for administering medicaments to patients
IT1204826B (it) 1986-03-04 1989-03-10 Chiesi Farma Spa Composizioni farmaceutiche per inalazione
GB9004781D0 (en) 1990-03-02 1990-04-25 Glaxo Group Ltd Device
US5780466A (en) * 1995-01-30 1998-07-14 Sanofi Substituted heterocyclic compounds method of preparing them and pharmaceutical compositions in which they are present
WO1998024788A1 (en) * 1996-12-02 1998-06-11 Georgetown University Tropane derivatives and method for their synthesis
US6248752B1 (en) * 1998-02-27 2001-06-19 Charles Duane Smith Azabicyclooctane compositions and methods for enhancing chemotherapy
US6262066B1 (en) * 1998-07-27 2001-07-17 Schering Corporation High affinity ligands for nociceptin receptor ORL-1
ES2165768B1 (es) 1999-07-14 2003-04-01 Almirall Prodesfarma Sa Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen.
SI1353919T1 (sl) * 2000-12-28 2006-12-31 Almirall Prodesfarma Ag Novi derivati kinuklidina in medicinske zmesi, kijih vsebujejo.
RU2004110717A (ru) * 2001-10-17 2005-10-20 Юсиби, С.А. (Be) Производные хинуклидина, способы их получения и их применение в качестве и нгибиторов м2- и/или м3- мускариновых рецепторов
JP2005510523A (ja) * 2001-11-09 2005-04-21 ファルマシア アンド アップジョン カンパニー リミティド ライアビリティー カンパニー アザ二環式フェニル縮合複素環式化合物、及びα7NACHRリガンドとしての当該化合物の使用
CA2470956C (en) * 2001-12-20 2011-08-02 Laboratorios S.A.L.V.A.T., S.A. 1-alkyl-1-azoniabicyclo[2.2.2]octane carbamate derivatives and their use as muscarinic receptor antagonists
US6696462B2 (en) * 2002-01-31 2004-02-24 Boehringer Ingelheim Pharma Gmbh & Co. Kg Anticholinergics, processes for the preparation thereof, and pharmaceutical compositions
ES2206021B1 (es) 2002-04-16 2005-08-01 Almirall Prodesfarma, S.A. Nuevos derivados de pirrolidinio.
ES2204295B1 (es) * 2002-07-02 2005-08-01 Almirall Prodesfarma, S.A. Nuevos derivados de quinuclidina-amida.
UY27927A1 (es) 2002-08-06 2003-12-31 Glaxo Group Ltd Antagonistas del receptor muscarínico m3 de acetilcolina
WO2004091482A2 (en) 2003-04-07 2004-10-28 Glaxo Group Limited M3 muscarinic acetylcholine receptor antagonists
PE20050711A1 (es) 2003-07-17 2005-09-10 Glaxo Group Ltd Compuestos 8-azoniabiciclo[3.2.1] octanos como antagonistas de los receptores muscarinicos de la acetilcolina
TW200519108A (en) 2003-07-17 2005-06-16 Glaxo Group Ltd Muscarinic acetylcholine receptor antagonists
PE20050327A1 (es) 2003-07-17 2005-06-08 Glaxo Group Ltd Derivados de 8-azoniabiciclo[3.2.1]octano como antagonistas de los receptores muscarinicos de la acetilcolina
CN101230061A (zh) 2003-10-14 2008-07-30 葛兰素集团有限公司 蕈毒碱性乙酰胆碱受体拮抗剂
MXPA06004242A (es) 2003-10-17 2006-06-28 Glaxo Group Ltd Antagonistas del receptor muscarinico de la acetilcolina.
TW200524577A (en) 2003-11-04 2005-08-01 Glaxo Group Ltd Muscarinic acetylcholine receptor antagonists
ES2329586T3 (es) * 2003-11-21 2009-11-27 Theravance, Inc. Compuestos que tienen actividad agonista del receptor beta2 adrenergico y antagonista del receptor muscarino.
UY28645A1 (es) 2003-12-03 2005-06-30 Glaxo Group Ltd Nuevos antagonistas del receptor muscarinico m3 de acetilcolina
PE20050861A1 (es) 2003-12-03 2005-12-10 Glaxo Group Ltd Derivados de sales ciclicas de amonio cuaternario como antagonistas del receptor muscarinico de acetilcolina
TW200534855A (en) 2004-01-13 2005-11-01 Glaxo Group Ltd Muscarinic acetylcholine receptor antagonists
WO2005086873A2 (en) 2004-03-11 2005-09-22 Glaxo Group Limited Novel m3 muscarinic acetylcholine receptor antagonists
WO2005087236A1 (en) 2004-03-11 2005-09-22 Glaxo Group Limited Novel m3 muscarinic acetylcholine receptor antagonists
WO2005094251A2 (en) 2004-03-17 2005-10-13 Glaxo Group Limited M3muscarinic acetylcholine receptor antagonists
WO2005095407A1 (en) 2004-03-17 2005-10-13 Glaxo Group Limited M3 muscarinic acetylcholine receptor antagonists
US20070185088A1 (en) 2004-03-17 2007-08-09 Jakob Busch-Petersen M3 muscarinic acetylchoine receptor antagonists
US20070185090A1 (en) 2004-03-17 2007-08-09 Jakob Busch-Petersen Muscarinic acetylchoine receptor antagonists
WO2005099706A2 (en) 2004-04-07 2005-10-27 Glaxo Group Limited Muscarinic acetylcholine receptor antagonists
AR050902A1 (es) 2004-04-27 2006-12-06 Glaxo Group Ltd Compuesto de quinuclidina, composicion farmaceutica que lo comprende y su usopara preparar dicha composicion
EP1747219A4 (en) 2004-05-13 2010-05-26 Glaxo Group Ltd Antagonists of muscarinic acetylcholine receptor
TW200606161A (en) 2004-05-28 2006-02-16 Glaxo Group Ltd Muscarinic acetylcholine receptor antagonists
WO2006005057A2 (en) 2004-06-30 2006-01-12 Glaxo Group Limited Muscarinic acetylcholine receptor antagonists
WO2006017768A2 (en) 2004-08-05 2006-02-16 Glaxo Group Limited Muscarinic acetylcholine receptor antagonists
WO2006017767A2 (en) 2004-08-06 2006-02-16 Glaxo Group Limited Muscarinic acetylcholine receptor antagonists
JP2008518939A (ja) 2004-10-29 2008-06-05 グラクソ グループ リミテッド ムスカリン性アセチルコリン受容体アンタゴニスト
WO2006055503A2 (en) 2004-11-15 2006-05-26 Glaxo Group Limited Novel m3 muscarinic acetylcholine receptor antagonists
JP2008520579A (ja) 2004-11-15 2008-06-19 グラクソ グループ リミテッド 新規m3ムスカリン性アセチルコリン受容体アンタゴニスト
PE20060826A1 (es) 2004-12-06 2006-10-08 Smithkline Beecham Corp Derivado oleofinico de 8-azoniabiciclo[3.2.1]octano y combinacion farmaceutica que lo comprende
PE20061162A1 (es) 2004-12-06 2006-10-14 Smithkline Beecham Corp Compuestos derivados olefinicos de 8-azoniabiciclo[3.2.1]octanos
WO2006065755A2 (en) 2004-12-13 2006-06-22 Glaxo Group Limited Quaternary ammonium salts of fused hetearomatic amines as novel muscarinic acetylcholine receptor antagonists
WO2006065788A2 (en) 2004-12-13 2006-06-22 Glaxo Group Limited Novel muscarinic acetylcholine receptor antagonists
WO2007018508A1 (en) 2005-07-28 2007-02-15 Glaxo Group Limited Novel m3 muscarinic acetycholine receptor antagonists
WO2007018514A1 (en) 2005-07-28 2007-02-15 Glaxo Group Limited Novel m3 muscarinic acetylcholine receptor antagonists
EP1937267A4 (en) 2005-08-02 2009-08-26 Glaxo Group Ltd M3-MUSCARIN ACETYLCHOLIN RECEPTOR ANTAGONISTS
WO2007016650A2 (en) 2005-08-02 2007-02-08 Glaxo Group Limited M3 muscarinic acetylcholine receptor antagonists
US7767691B2 (en) 2005-08-18 2010-08-03 Glaxo Group Limited Muscarinic acetylcholine receptor antagonists containing an azoniabiocyclo[2.2.1] heptane ring system
GB0921075D0 (en) * 2009-12-01 2010-01-13 Glaxo Group Ltd Novel combination of the therapeutic agents

Also Published As

Publication number Publication date
AP2006003746A0 (en) 2006-10-31
JP5014121B2 (ja) 2012-08-29
EP1740177B1 (en) 2012-08-08
UA95768C2 (ru) 2011-09-12
PT1740177E (pt) 2012-11-02
US20140371264A1 (en) 2014-12-18
EA021994B1 (ru) 2015-10-30
ECSP066940A (es) 2006-12-20
AU2005237576A1 (en) 2005-11-10
UY28871A1 (es) 2005-11-30
EP1740177A4 (en) 2010-05-05
KR101037026B1 (ko) 2011-05-25
SI2570128T1 (sl) 2016-11-30
SG186597A1 (en) 2013-01-30
US9045469B2 (en) 2015-06-02
US20090124653A1 (en) 2009-05-14
CA2564742C (en) 2012-01-10
PL2570128T3 (pl) 2017-09-29
BRPI0510170B8 (pt) 2021-05-25
EA201100019A1 (ru) 2011-12-30
FR14C0075I2 (fr) 2015-05-22
LU92565I9 (enExample) 2019-01-17
IL178152A0 (en) 2006-12-31
EP3111936A1 (en) 2017-01-04
AP2213A (en) 2011-03-01
BE2014C063I2 (enExample) 2024-08-08
FR14C0075I1 (fr) 2014-11-21
WO2005104745A3 (en) 2006-08-03
DK1740177T3 (da) 2012-10-29
NL300694I2 (enExample) 2015-12-29
SI1740177T1 (sl) 2012-12-31
CY2014043I2 (el) 2015-12-09
CY1118082T1 (el) 2017-06-28
TW200605887A (en) 2006-02-16
ES2600405T3 (es) 2017-02-08
EA015033B1 (ru) 2011-04-29
JP2012162559A (ja) 2012-08-30
CN1976701A (zh) 2007-06-06
MA28631B1 (fr) 2007-06-01
CN102040602A (zh) 2011-05-04
WO2005104745A2 (en) 2005-11-10
DK2570128T3 (en) 2016-11-07
ES2392848T3 (es) 2012-12-14
LU92565I2 (fr) 2014-12-02
ZA200608565B (en) 2019-12-18
US7498440B2 (en) 2009-03-03
US20160002220A1 (en) 2016-01-07
HRP20120832T1 (hr) 2012-11-30
US20070185155A1 (en) 2007-08-09
NZ549997A (en) 2010-10-29
IL178152A (en) 2011-05-31
US20070249664A1 (en) 2007-10-25
US20140080863A1 (en) 2014-03-20
CY1113196T1 (el) 2015-12-09
US8575347B2 (en) 2013-11-05
JP5398871B2 (ja) 2014-01-29
PT2570128T (pt) 2016-10-07
US20130030015A1 (en) 2013-01-31
LT2570128T (lt) 2016-10-10
ES2392848T4 (es) 2014-10-01
NO2017018I2 (no) 2018-05-14
TWI363759B (en) 2012-05-11
US20120157491A1 (en) 2012-06-21
NO2017018I1 (no) 2017-05-04
NO2017017I1 (no) 2017-05-04
NO338959B1 (no) 2016-11-07
US7488827B2 (en) 2009-02-10
BRPI0510170A (pt) 2007-10-02
US8853404B2 (en) 2014-10-07
CA2755954A1 (en) 2005-11-10
EP1740177A2 (en) 2007-01-10
HRP20161385T1 (hr) 2016-12-02
CA2564742A1 (en) 2005-11-10
US9144571B2 (en) 2015-09-29
KR20110010841A (ko) 2011-02-07
HK1102423A1 (en) 2007-11-23
HUE031304T2 (hu) 2017-07-28
KR20070015412A (ko) 2007-02-02
PL1740177T3 (pl) 2012-12-31
NL300694I1 (enExample) 2015-12-29
PE20060259A1 (es) 2006-03-25
NO20065417L (no) 2006-12-29
CY2014043I1 (el) 2015-12-09
US20150238470A1 (en) 2015-08-27
US8183257B2 (en) 2012-05-22
EP2570128B1 (en) 2016-08-10
US8309572B2 (en) 2012-11-13
EP2570128A1 (en) 2013-03-20
HUS1400053I1 (hu) 2017-07-28
BRPI0510170B1 (pt) 2018-12-18
KR101152032B1 (ko) 2012-06-11
JP2007534769A (ja) 2007-11-29
AR050902A1 (es) 2006-12-06
MY144753A (en) 2011-10-31
MXPA06012405A (es) 2007-01-17
AU2005237576B2 (en) 2012-01-12
EA200601991A1 (ru) 2007-02-27

Similar Documents

Publication Publication Date Title
AU2005237576B2 (en) Muscarinic Acetylcholine Receptor Antagonists
US7767691B2 (en) Muscarinic acetylcholine receptor antagonists containing an azoniabiocyclo[2.2.1] heptane ring system
US7598267B2 (en) Muscarinic acetylcholine receptor antagonists
AU2012202307B2 (en) Muscarinic acetylcholine receptor antagonists
HK1102423B (en) Muscarinic acetylcholine receptor antagonists

Legal Events

Date Code Title Description
EEER Examination request
R00 Party data change recorded

Free format text: ST27 STATUS EVENT CODE: A-4-4-R10-R00-R113 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: CHANGE OF ADDRESS OR METHOD OF CORRESPONDENCE REQUEST RECEIVED

Effective date: 20250422

R18 Changes to party contact information recorded

Free format text: ST27 STATUS EVENT CODE: A-4-4-R10-R18-R143 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: CHANGE OF ADDRESS REQUIREMENTS DETERMINED COMPLIANT

Effective date: 20260511

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W111 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: CORRESPONDENT DETERMINED COMPLIANT

Effective date: 20260511