GB1219606A - Quinuclidinol derivatives and preparation thereof - Google Patents
Quinuclidinol derivatives and preparation thereofInfo
- Publication number
- GB1219606A GB1219606A GB33654/68A GB3365468A GB1219606A GB 1219606 A GB1219606 A GB 1219606A GB 33654/68 A GB33654/68 A GB 33654/68A GB 3365468 A GB3365468 A GB 3365468A GB 1219606 A GB1219606 A GB 1219606A
- Authority
- GB
- United Kingdom
- Prior art keywords
- quinuclidinol
- compounds
- thienyl
- july
- preparation
- 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
Links
- FSNYTEYOTCTPSO-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-2-ol Chemical class C1CN2C(O)CC1CC2 FSNYTEYOTCTPSO-UHFFFAOYSA-N 0.000 title 1
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 9-xanthyl Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000001544 thienyl group Chemical group 0.000 abstract 2
- 229930003347 Atropine Natural products 0.000 abstract 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 abstract 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002921 anti-spasmodic effect Effects 0.000 abstract 1
- 229940124575 antispasmodic agent Drugs 0.000 abstract 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 abstract 1
- 229960000396 atropine Drugs 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 239000000812 cholinergic antagonist Substances 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
Classifications
-
- 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
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01B—MEASURING LENGTH, THICKNESS OR SIMILAR LINEAR DIMENSIONS; MEASURING ANGLES; MEASURING AREAS; MEASURING IRREGULARITIES OF SURFACES OR CONTOURS
- G01B13/00—Measuring arrangements characterised by the use of fluids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Emergency Medicine (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33654/68A GB1219606A (en) | 1968-07-15 | 1968-07-15 | Quinuclidinol derivatives and preparation thereof |
| BE735031D BE735031A (https=) | 1968-07-15 | 1969-06-23 | |
| CH983469A CH513174A (fr) | 1968-07-15 | 1969-06-25 | Procédé pour la préparation de dérivés du quinuclidinol |
| FR6923465A FR2012964A1 (https=) | 1968-07-15 | 1969-07-10 | |
| SE09934/69A SE361314B (https=) | 1968-07-15 | 1969-07-14 | |
| DE19691935751 DE1935751A1 (de) | 1968-07-15 | 1969-07-14 | Neue Chinuclidinolderivate,Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Arzneipraeparaten |
| US00841970A US3714357A (en) | 1968-07-15 | 1969-07-15 | Pharmaceutical compositions comprising quinuclidinol derivatives |
| AT680869A AT291272B (de) | 1968-07-15 | 1969-07-15 | Verfahren zur Herstellung von neuen Chinuclidinolderivaten, ihren Salzen und quartären Ammoniumsalzen |
| NL696910859A NL148607B (nl) | 1968-07-15 | 1969-07-15 | Werkwijze voor het bereiden van geneesmiddelen met antispasmodische en anticholinergische activiteit welke als actief bestanddeel een 3-chinuclidinolester bevatten, aldus bereide gevormde geneesmiddelen, alsmede een werkwijze voor het bereiden van de actieve verbindingen. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33654/68A GB1219606A (en) | 1968-07-15 | 1968-07-15 | Quinuclidinol derivatives and preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1219606A true GB1219606A (en) | 1971-01-20 |
Family
ID=10355712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB33654/68A Expired GB1219606A (en) | 1968-07-15 | 1968-07-15 | Quinuclidinol derivatives and preparation thereof |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3714357A (https=) |
| AT (1) | AT291272B (https=) |
| BE (1) | BE735031A (https=) |
| CH (1) | CH513174A (https=) |
| DE (1) | DE1935751A1 (https=) |
| FR (1) | FR2012964A1 (https=) |
| GB (1) | GB1219606A (https=) |
| NL (1) | NL148607B (https=) |
| SE (1) | SE361314B (https=) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0036218A3 (en) * | 1980-03-19 | 1981-12-30 | D And D S.R.L. | Quinuclidinic esters and derivatives of phenoxycarboxylic acids, a process for the preparation thereof, and related pharmaceutical compositions |
| US6750226B2 (en) | 1999-07-14 | 2004-06-15 | Almirall-Prodesfarma, S.A. | Quinuclidine derivatives and their use as muscarinic M3 receptor ligands |
| JP2005533826A (ja) * | 2002-07-02 | 2005-11-10 | アルミラール・プロデスファルマ・アクチェンゲゼルシャフト | 新規なるキヌクリジンアミド誘導体 |
| US7122558B2 (en) | 2000-12-28 | 2006-10-17 | Almirall Prodesfarma Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| US7214687B2 (en) | 1999-07-14 | 2007-05-08 | Almirall Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| US8044205B2 (en) | 2006-07-21 | 2011-10-25 | Laboratorios Almirall, S.A. | Process for manufacturing 3(R)-(2-hydroxy-2,2-dithien-2-ylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide |
| US9254262B2 (en) | 2008-03-13 | 2016-02-09 | Almirall, S.A. | Dosage and formulation |
| US9737520B2 (en) | 2011-04-15 | 2017-08-22 | Almirall, S.A. | Aclidinium for use in improving the quality of sleep in respiratory patients |
| US10085974B2 (en) | 2008-03-13 | 2018-10-02 | Almirall, S.A. | Dosage and formulation |
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2155927A1 (en) * | 1971-10-15 | 1973-05-25 | Synthelabo | 1-phenylcyclo hexane carboxylic acid esters - with antispasmodic and anticholinergic activity |
| EP0052645B1 (en) * | 1980-06-03 | 1987-05-13 | Research Corporation | Gamma-emitting receptor-binding quinuclidinyl benzilates methods of preparation thereof and imaging and assay methods utilizing same |
| US4431627A (en) * | 1980-06-03 | 1984-02-14 | Research Corporation | Gamma-emitting receptor-binding 3-quinuclidinyl glycolates; methods of preparation thereof and imaging and assay methods utilizing same |
| US4644003A (en) * | 1985-04-03 | 1987-02-17 | Research Corporation | 3-quinuclidinol esters, useful as antagonists of muscarinic acetylcholine receptors |
| GB8923590D0 (en) * | 1989-10-19 | 1989-12-06 | Pfizer Ltd | Antimuscarinic bronchodilators |
| CA2073005C (en) * | 1990-09-06 | 1998-11-10 | Alan Stobie | Antimuscarinic bronchodilators |
| WO1998000139A1 (en) * | 1996-07-01 | 1998-01-08 | Sepracor, Inc. | Methods and compositions for treating urinary incontinence using enantiomerically enriched (s)-clidinium |
| WO1998000138A1 (en) * | 1996-07-01 | 1998-01-08 | Sepracor, Inc. | Methods and compositions for treating urinary incontinence using enantiomerically enriched (r)-clidinium |
| JP4445704B2 (ja) | 2000-12-22 | 2010-04-07 | アルミラル・ソシエダッド・アノニマ | キヌクリジンカルバメート誘導体およびｍ３アンダゴニストとしてのそれらの使用 |
| ES2206021B1 (es) * | 2002-04-16 | 2005-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de pirrolidinio. |
| ES2203327B1 (es) * | 2002-06-21 | 2005-06-16 | Almirall Prodesfarma, S.A. | Nuevos carbamatos de quinuclidina y composiciones farmaceuticas que los contienen. |
| TW200519106A (en) | 2003-05-02 | 2005-06-16 | Novartis Ag | Organic compounds |
| AR044134A1 (es) * | 2003-05-02 | 2005-08-24 | Novartis Ag | Derivados de quinuclidina, metodo de preparacion y composiciones farmaceuticas. |
| GB0401334D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
| ES2239546B1 (es) * | 2004-03-15 | 2006-12-01 | Almirall Prodesfarma, S.A. | Nuevos esteres de quinuclidina cuaternizados. |
| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| ES2257152B1 (es) * | 2004-05-31 | 2007-07-01 | Laboratorios Almirall S.A. | Combinaciones que comprenden agentes antimuscarinicos y agonistas beta-adrenergicos. |
| ES2246170B1 (es) * | 2004-07-29 | 2007-04-01 | Almirall Prodesfarma, S.A. | Nuevo procedimiento para preparar derivados de carbamato de quinuclidinio. |
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
| GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| RU2421464C2 (ru) | 2005-10-21 | 2011-06-20 | Новартис Аг | Человеческие антитела к il-13 и их терапевтическое применение |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| EP2322525B1 (en) | 2006-04-21 | 2013-09-18 | Novartis AG | Purine derivatives for use as adenosin A2A receptor agonists |
| WO2008037477A1 (en) | 2006-09-29 | 2008-04-03 | Novartis Ag | Pyrazolopyrimidines as p13k lipid kinase inhibitors |
| PL2104535T3 (pl) | 2007-01-10 | 2011-05-31 | Irm Llc | Związki i kompozycje jako inhibitory proteazy aktywujące kanały |
| DE602008005140D1 (de) | 2007-05-07 | 2011-04-07 | Novartis Ag | Organische verbindungen |
| CA2608561A1 (en) * | 2007-10-29 | 2009-04-29 | Carl Paluszkiewicz | Motorcycle wind deflector accessory support |
| MX2010006421A (es) | 2007-12-10 | 2010-06-25 | Novartis Ag | Compuestos organicos. |
| MX2010007604A (es) | 2008-01-11 | 2010-08-02 | Novartis Ag | Pirimidinas como inhibidores de cinasa. |
| US8268834B2 (en) | 2008-03-19 | 2012-09-18 | Novartis Ag | Pyrazine derivatives that inhibit phosphatidylinositol 3-kinase enzyme |
| JP2011522860A (ja) | 2008-06-10 | 2011-08-04 | ノバルティス アーゲー | 上皮性ナトリウムチャネルブロッカーとしてのピラジン誘導体 |
| PT2391366E (pt) | 2009-01-29 | 2013-02-05 | Novartis Ag | Benzimidazoles substituídos para o tratamento de astrocitomas |
| US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
| JP5781510B2 (ja) | 2009-08-12 | 2015-09-24 | ノバルティス アーゲー | ヘテロ環式ヒドラゾン化合物および癌および炎症の処置のためのそれらの使用 |
| PE20121148A1 (es) | 2009-08-17 | 2012-09-07 | Intellikine Llc | Compuestos heterociclicos y usos de los mismos |
| JP5775871B2 (ja) | 2009-08-20 | 2015-09-09 | ノバルティス アーゲー | ヘテロ環式オキシム化合物 |
| MX2012004792A (es) | 2009-10-22 | 2013-02-01 | Vertex Pharma | Composiciones para el tratamiento de fibrosis quistica y otras enfermedades cronicas. |
| US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| US8637516B2 (en) | 2010-09-09 | 2014-01-28 | Irm Llc | Compounds and compositions as TRK inhibitors |
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| US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
| WO2012107500A1 (en) | 2011-02-10 | 2012-08-16 | Novartis Ag | [1, 2, 4] triazolo [4, 3 -b] pyridazine compounds as inhibitors of the c-met tyrosine kinase |
| WO2012116237A2 (en) | 2011-02-23 | 2012-08-30 | Intellikine, Llc | Heterocyclic compounds and uses thereof |
| WO2012116217A1 (en) | 2011-02-25 | 2012-08-30 | Irm Llc | Compounds and compositions as trk inhibitors |
| US8883819B2 (en) | 2011-09-01 | 2014-11-11 | Irm Llc | Bicyclic heterocycle derivatives for the treatment of pulmonary arterial hypertension |
| EA026655B1 (ru) | 2011-09-15 | 2017-05-31 | Новартис Аг | 6-ЗАМЕЩЕННЫЕ 3-(ХИНОЛИН-6-ИЛТИО)[1,2,4]ТРИАЗОЛО[4,3-a]ПИРИДИНЫ В КАЧЕСТВЕ ИНГИБИТОРОВ c-MET ТИРОЗИНКИНАЗЫ |
| WO2013038373A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| CN103946221B (zh) | 2011-09-16 | 2016-08-03 | 诺华股份有限公司 | 用于治疗囊性纤维化的杂环化合物 |
| WO2013038378A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
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| CA2856803A1 (en) | 2011-11-23 | 2013-05-30 | Intellikine, Llc | Enhanced treatment regimens using mtor inhibitors |
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| JP2015512425A (ja) | 2012-04-03 | 2015-04-27 | ノバルティス アーゲー | チロシンキナーゼ阻害剤との組合せ製品及びそれらの使用 |
| US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
| EP2968340A4 (en) | 2013-03-15 | 2016-08-10 | Intellikine Llc | COMBINING KINASE INHIBITORS AND USES THEREOF |
| EP3023424B1 (en) | 2013-07-13 | 2019-02-27 | Beijing Shuobai Pharmaceutical Co., Ltd. | Quinine compounds, and optical isomers, preparation method and medical use thereof |
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| EP3134397A1 (en) | 2014-04-24 | 2017-03-01 | Novartis AG | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| KR20160145780A (ko) | 2014-04-24 | 2016-12-20 | 노파르티스 아게 | 포스파티딜이노시톨 3-키나제 억제제로서의 아미노 피리딘 유도체 |
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| WO2016011658A1 (en) | 2014-07-25 | 2016-01-28 | Novartis Ag | Combination therapy |
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| WO2020250116A1 (en) | 2019-06-10 | 2020-12-17 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of cf, copd, and bronchiectasis |
| PE20220346A1 (es) | 2019-08-28 | 2022-03-14 | Novartis Ag | Derivados de 1,3-fenil heteroarilo sustituidos y su uso en el tratamiento de enfermedades |
| TW202140550A (zh) | 2020-01-29 | 2021-11-01 | 瑞士商諾華公司 | 使用抗ｔｓｌｐ抗體治療炎性或阻塞性氣道疾病之方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3252981A (en) * | 1963-05-24 | 1966-05-24 | Chemetron Corp | Process for benzilic esters |
-
1968
- 1968-07-15 GB GB33654/68A patent/GB1219606A/en not_active Expired
-
1969
- 1969-06-23 BE BE735031D patent/BE735031A/xx unknown
- 1969-06-25 CH CH983469A patent/CH513174A/fr not_active IP Right Cessation
- 1969-07-10 FR FR6923465A patent/FR2012964A1/fr not_active Withdrawn
- 1969-07-14 DE DE19691935751 patent/DE1935751A1/de active Pending
- 1969-07-14 SE SE09934/69A patent/SE361314B/xx unknown
- 1969-07-15 US US00841970A patent/US3714357A/en not_active Expired - Lifetime
- 1969-07-15 AT AT680869A patent/AT291272B/de not_active IP Right Cessation
- 1969-07-15 NL NL696910859A patent/NL148607B/xx not_active IP Right Cessation
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0036218A3 (en) * | 1980-03-19 | 1981-12-30 | D And D S.R.L. | Quinuclidinic esters and derivatives of phenoxycarboxylic acids, a process for the preparation thereof, and related pharmaceutical compositions |
| US9333195B2 (en) | 1999-07-14 | 2016-05-10 | Almirall, S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| US10034867B2 (en) | 1999-07-14 | 2018-07-31 | Almirall, S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| US7078412B2 (en) | 1999-07-14 | 2006-07-18 | Almirall Prodesfarma Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| US7109210B2 (en) | 1999-07-14 | 2006-09-19 | Almirall Prodesfarma Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| US10588895B2 (en) | 1999-07-14 | 2020-03-17 | Almirall, S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| US7196098B2 (en) | 1999-07-14 | 2007-03-27 | Almirall Prodesfarma Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| US7214687B2 (en) | 1999-07-14 | 2007-05-08 | Almirall Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| US7750023B2 (en) | 1999-07-14 | 2010-07-06 | Almirall, S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| US8513279B2 (en) | 1999-07-14 | 2013-08-20 | Almirall, S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| US9687478B2 (en) | 1999-07-14 | 2017-06-27 | Almirall, S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| US7897617B2 (en) | 1999-07-14 | 2011-03-01 | Almirall Prodesfarma S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| USRE46417E1 (en) | 1999-07-14 | 2017-05-30 | Almirall, S.A. | Quinuclidine derivatives and their use as muscarinic M3 receptor ligands |
| US6750226B2 (en) | 1999-07-14 | 2004-06-15 | Almirall-Prodesfarma, S.A. | Quinuclidine derivatives and their use as muscarinic M3 receptor ligands |
| US8802699B2 (en) | 1999-07-14 | 2014-08-12 | Almirall, S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| US8129405B2 (en) | 1999-07-14 | 2012-03-06 | Almirall Prodesfarma S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| US9056100B2 (en) | 1999-07-14 | 2015-06-16 | Almirall, S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| US7893087B2 (en) | 2000-12-28 | 2011-02-22 | Almirall, S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| US7879874B2 (en) | 2000-12-28 | 2011-02-01 | Almirall, S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
| US7122558B2 (en) | 2000-12-28 | 2006-10-17 | Almirall Prodesfarma Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| JP2005533826A (ja) * | 2002-07-02 | 2005-11-10 | アルミラール・プロデスファルマ・アクチェンゲゼルシャフト | 新規なるキヌクリジンアミド誘導体 |
| US8044205B2 (en) | 2006-07-21 | 2011-10-25 | Laboratorios Almirall, S.A. | Process for manufacturing 3(R)-(2-hydroxy-2,2-dithien-2-ylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide |
| US9254262B2 (en) | 2008-03-13 | 2016-02-09 | Almirall, S.A. | Dosage and formulation |
| US10085974B2 (en) | 2008-03-13 | 2018-10-02 | Almirall, S.A. | Dosage and formulation |
| US11000517B2 (en) | 2008-03-13 | 2021-05-11 | Almirall, S.A. | Dosage and formulation |
| US9737520B2 (en) | 2011-04-15 | 2017-08-22 | Almirall, S.A. | Aclidinium for use in improving the quality of sleep in respiratory patients |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2012964A1 (https=) | 1970-03-27 |
| NL6910859A (https=) | 1970-01-19 |
| NL148607B (nl) | 1976-02-16 |
| AT291272B (de) | 1971-07-12 |
| SE361314B (https=) | 1973-10-29 |
| CH513174A (fr) | 1971-09-30 |
| US3714357A (en) | 1973-01-30 |
| BE735031A (https=) | 1969-12-01 |
| DE1935751A1 (de) | 1970-02-26 |
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