ES2699507T3 - Composición farmacéutica que comprende una suspensión acuosa de un derivado de androstano para el tratamiento de afecciones inflamatorias y alérgicas - Google Patents
Composición farmacéutica que comprende una suspensión acuosa de un derivado de androstano para el tratamiento de afecciones inflamatorias y alérgicas Download PDFInfo
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- ES2699507T3 ES2699507T3 ES03737365T ES03737365T ES2699507T3 ES 2699507 T3 ES2699507 T3 ES 2699507T3 ES 03737365 T ES03737365 T ES 03737365T ES 03737365 T ES03737365 T ES 03737365T ES 2699507 T3 ES2699507 T3 ES 2699507T3
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- A61K9/0043—Nose
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- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/44—Glucocorticosteroids; Drugs increasing or potentiating the activity of glucocorticosteroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Otolaryngology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pulmonology (AREA)
- Dispersion Chemistry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/067,020 US6858596B2 (en) | 2000-08-05 | 2002-02-04 | Formulation containing anti-inflammatory androstane derivative |
| PCT/GB2003/000504 WO2003066024A1 (en) | 2002-02-04 | 2003-02-04 | Pharmaceutical formulation comprising an aqueous suspension of an androstane derivative for the treatment of inflammatory and allergic conditions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2699507T3 true ES2699507T3 (es) | 2019-02-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03737365T Expired - Lifetime ES2699507T3 (es) | 2002-02-04 | 2003-02-04 | Composición farmacéutica que comprende una suspensión acuosa de un derivado de androstano para el tratamiento de afecciones inflamatorias y alérgicas |
Country Status (6)
| Country | Link |
|---|---|
| US (5) | US6858596B2 (enExample) |
| EP (2) | EP3510994A1 (enExample) |
| JP (1) | JP4838493B2 (enExample) |
| AU (1) | AU2003244506A1 (enExample) |
| ES (1) | ES2699507T3 (enExample) |
| WO (1) | WO2003066024A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6777399B2 (en) * | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| SI1305329T2 (sl) | 2000-08-05 | 2015-07-31 | Glaxo Group Limited | S-fluorometil ester 6alfa,9alfa-difluoro-17alfa-(2-furanilkarboksil)oksi-11beta-hidroksi- 16alfa-metil-3-okso-androst-1,4-dien-17-karbotiojske kisline kot protivnetno sredstvo |
| GB0019172D0 (en) | 2000-08-05 | 2000-09-27 | Glaxo Group Ltd | Novel compounds |
| US6787532B2 (en) * | 2000-08-05 | 2004-09-07 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivatives |
| US6858596B2 (en) * | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| US6759398B2 (en) * | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| UA77656C2 (en) | 2001-04-07 | 2007-01-15 | Glaxo Group Ltd | S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent |
| DE10119718A1 (de) * | 2001-04-21 | 2002-10-31 | Boehringer Ingelheim Pharma | Verfahren zur kontinuierlichen Herstellung inhalierfähiger Arzneistoffe, Vorrichtung zur Durchführung des Verfahrens und nach diesem Verfahren hergestellter Arzneistoff |
| CA2445839A1 (en) * | 2001-04-30 | 2002-11-07 | Glaxo Group Limited | Anti-inflammatory 17.beta.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.alpha |
| JP2005500290A (ja) * | 2001-06-12 | 2005-01-06 | グラクソ グループ リミテッド | 抗炎症性の、１７β−カルボチオアートアンドロスタン誘導体である１７α複素環エステル |
| GB0125259D0 (en) * | 2001-10-20 | 2001-12-12 | Glaxo Group Ltd | Novel compounds |
| US20050175545A1 (en) * | 2002-02-04 | 2005-08-11 | Keith Biggadike | Formulation for inhalation comprising a glucocorticoid and a beta 2-adrenoreceptor agonist |
| GB0202635D0 (en) * | 2002-02-05 | 2002-03-20 | Glaxo Wellcome Mfg Pte Ltd | Formulation containing novel anti-inflammatory androstane derivative |
| GB2389530B (en) | 2002-06-14 | 2007-01-10 | Cipla Ltd | Pharmaceutical compositions |
| GB0507165D0 (en) * | 2005-04-08 | 2005-05-18 | Glaxo Group Ltd | Novel crystalline pharmaceutical product |
| GB0615108D0 (en) * | 2006-07-28 | 2006-09-06 | Glaxo Group Ltd | Novel formulations |
| WO2009150101A1 (en) * | 2008-06-09 | 2009-12-17 | Glaxo Group Limited | Pharmaceutical compositions comprising n-[2-((2r)-2-{[4-[(4-chlorophenyl)methyl]-l-oxo-2(ih)-phthalaz inyl]methyl}-l- pyrrolidinyl)ethyl]-4-(methyloxy)butanamide |
| US8642069B2 (en) * | 2008-08-27 | 2014-02-04 | Alexander D. Goldin | Composition and method for treating colds |
| ES2417339T3 (es) | 2009-04-23 | 2013-08-07 | Theravance, Inc. | Compuestos de diamina que tienen actividad antagonista del receptor muscarinico y agonista del receptor beta2-adrenergico |
| US9290698B2 (en) | 2010-07-15 | 2016-03-22 | Battelle Memorial Institute | Biobased polyols for potential use as flame retardants in polyurethane and polyester applications |
| AR083115A1 (es) | 2010-09-30 | 2013-01-30 | Theravance Inc | Sales oxalato cristalinas de un compuesto diamida |
| US8658676B2 (en) | 2010-10-12 | 2014-02-25 | The Medicines Company | Clevidipine emulsion formulations containing antimicrobial agents |
| HUE026295T2 (en) | 2010-10-12 | 2016-06-28 | The Medicines Co | Clevidipine emulsion formulations containing antimicrobial agents |
| DE102011103347B4 (de) * | 2011-05-27 | 2014-10-30 | Meda Pharma Gmbh & Co. Kg | Nasale pharmazeutische Formulierung |
| EA201791738A1 (ru) * | 2012-05-09 | 2018-03-30 | Вестерн Юниверсити Оф Хелт Сайенсиз | Пролипосомальные композиции тестостерона |
| WO2014095602A1 (en) * | 2012-12-17 | 2014-06-26 | Glaxo Group Limited | Combination of levocabastine and fluticasone furoate for the treatment of inflammatory and/or allergic conditions |
| WO2015008205A2 (en) * | 2013-07-13 | 2015-01-22 | Mahesh Kandula | Compositions and methods for the treatment of respiratory diseases |
| WO2018049184A1 (en) | 2016-09-09 | 2018-03-15 | Cutispharma, Inc. | Suspensions and diluents for metronidazole and baclofen |
| JPWO2019235616A1 (ja) | 2018-06-08 | 2021-06-17 | 東興薬品工業株式会社 | フルチカゾンフランカルボン酸エステル点鼻組成物 |
| JP7470646B2 (ja) | 2018-06-14 | 2024-04-18 | アストラゼネカ・ユーケイ・リミテッド | コルチコステロイド医薬組成物を用いて喘息の症状を治療および予防するための方法 |
Family Cites Families (155)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR580494A (fr) | 1923-07-10 | 1924-11-07 | Const Metalliques Schiltigheim | Procédé d'établissement des buses d'aération ou autres tuyaux |
| US2837464A (en) * | 1955-01-11 | 1958-06-03 | Schering Corp | Process for production of dienes by corynebacteria |
| DE1059906B (de) | 1954-10-05 | 1959-06-25 | Scherico Ltd | Verfahren zur Herstellung von 1, 4-Pregnadienen |
| US3067197A (en) | 1961-04-26 | 1962-12-04 | Pfizer & Co C | 11-oxygenated 6alpha-fluoro-16-methylene-delta-pregnenes and derivatives |
| GB1047518A (en) * | 1963-06-11 | 1966-11-02 | Glaxo Lab Ltd | 17ª-monoesters of 11,17,21-trihydroxy steroid compounds |
| GB1159490A (en) * | 1966-02-09 | 1969-07-23 | Boots Pure Drug Co Ltd | Improvements in Acylated Steroids |
| US3639434A (en) | 1967-02-02 | 1972-02-01 | Boots Pure Drug Co Ltd | 17-acyloxysteroids and their manufacture |
| IT1061787B (it) | 1967-03-01 | 1983-04-30 | Vismara Francesco Spa | Miglioramenti relativi alla preparazione di 17 benzoato di betametazone |
| GB1227992A (enExample) * | 1968-01-23 | 1971-04-15 | Koninklijke Gist Spiritus | |
| US3557694A (en) * | 1969-04-21 | 1971-01-26 | Burroughs Corp | Print head latching mechanism |
| IT1034011B (it) * | 1969-06-26 | 1979-09-10 | Vister Vismara Terapeutici S P | Processo per la prapratzione di 17 monoesteri di 17 a 21 diossisteroidi per idrolisi die corpispondenti 17 21 ortoesteri ciclici a ph control lato |
| GB1384372A (en) | 1971-01-20 | 1975-02-19 | Glaxo Lab Ltd | Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids |
| US3828080A (en) | 1972-01-20 | 1974-08-06 | Glaxo Lab Ltd | Androstane-17beta-carboxylic acids and processes for the preparation thereof |
| US3989686A (en) | 1972-06-15 | 1976-11-02 | Glaxo Laboratories Limited | Anaesthetic steroids of the androstane series and process for preparing same |
| GB1438940A (en) | 1972-07-19 | 1976-06-09 | Glaxo Lab Ltd | 17beta-haloalkoxycarbonyl-17alpha-oxysteroids |
| GB1440063A (en) * | 1972-08-11 | 1976-06-23 | Glaxo Lab Ltd | 17alpha-esters of 17alpha,21-dihydroxy-20-oxo-steroids |
| US3881894A (en) * | 1972-10-05 | 1975-05-06 | George R Onufer | Vapor emission control system and method |
| DE2336693A1 (de) | 1973-07-19 | 1975-02-06 | Nassheuer Ind Ofenbau Jean | Strahlheizrohr |
| US4093721A (en) | 1974-08-30 | 1978-06-06 | Glaxo Laboratories Limited | Pharmaceutical compositions of 6α,9α-difluoro-androst-4-ene-17β-carboxylates and derivatives thereof |
| GB1517278A (en) | 1974-08-30 | 1978-07-12 | Glaxo Lab Ltd | Alkyl and haloalkyl androsta-1,4,15-triene and-4,15-diene-17beta-carboxylates |
| US3969686A (en) * | 1975-03-26 | 1976-07-13 | Xerox Corporation | Beam collimation using multiple coupled elements |
| YU54476A (en) * | 1975-03-31 | 1982-05-31 | Taisho Pharmaceutical Co Ltd | Process for obtaining 17-ester 21-halo-pregnane |
| DE2538569A1 (de) | 1975-08-29 | 1977-03-03 | Siemens Ag | Verfahren zur metallisierung von duroplasten |
| CH628355A5 (de) | 1976-02-24 | 1982-02-26 | Ciba Geigy Ag | Verfahren zur herstellung neuer androstadien-17beta-carbonsaeuren und ihrer ester und salze. |
| US4221787A (en) * | 1978-03-28 | 1980-09-09 | Interx Research Corporation | Esteramide prodrugs of anti-inflammatory corticosteroids |
| US4188385A (en) | 1978-04-05 | 1980-02-12 | Syntex (U.S.A.) Inc. | Thioetianic acid derivatives |
| US4198403A (en) | 1978-04-05 | 1980-04-15 | Syntex (U.S.A.) Inc. | 17 Beta-thiocarboxylic acid esters of 4-halo-3-oxoandrost-4-enes |
| US4263289A (en) | 1978-04-05 | 1981-04-21 | Syntex (U.S.A.) Inc. | Thio etianic acid derivatives |
| US4187301A (en) | 1978-04-05 | 1980-02-05 | Syntex (U.S.A.) Inc. | 17 Beta-thiocarboxylic acid esters of 6 alpha, 6 beta-difluoro-3-oxoandrost-4-enes |
| US4261984A (en) | 1978-04-05 | 1981-04-14 | Syntex (U.S.A.) Inc. | 17β-thiocarboxylic acid esters of 3-oxo-4-halo-16β-methylandrost-4-enes |
| DE2817988A1 (de) * | 1978-04-25 | 1979-11-08 | Hoechst Ag | Corticoid 17-alkylcarbonate und verfahren zu deren herstellung |
| US4310466A (en) | 1979-08-31 | 1982-01-12 | Syntex (U.S.A.) Inc. | Thio etianic acid derivatives |
| US4267173A (en) | 1979-11-05 | 1981-05-12 | Schering Corporation | Use of 6β-fluoro-7α-halogenocorticoids as topical anti-inflammatories and pharmaceutical formulations useful therefor |
| US4377389A (en) | 1979-12-12 | 1983-03-22 | Foster Grant Corporation | Dip dyeing of plastic articles and the dye bath composition thereof |
| CY1291A (en) | 1980-02-15 | 1985-10-18 | Glaxo Group Ltd | Androstane 17 beta carbothioates |
| CA1201114A (en) | 1980-02-15 | 1986-02-25 | Gordon H. Phillipps | Androstane carbothioates |
| US4996335A (en) | 1980-07-10 | 1991-02-26 | Nicholas S. Bodor | Soft steroids having anti-inflammatory activity |
| ZA814440B (en) | 1980-07-10 | 1982-10-27 | Otsuka Pharma Co Ltd | Soft steroids having anti-inflammatory activity |
| SE449106B (sv) | 1980-07-10 | 1987-04-06 | Otsuka Pharma Co Ltd | Steroid med anti-inflammatorisk verkan samt komposition innehallande denna |
| US4710495A (en) | 1980-07-10 | 1987-12-01 | Otsuka Pharmaceutical Co., Ltd. | Soft steroids having anti-inflammatory activity |
| DE3260474D1 (en) | 1981-02-02 | 1984-09-06 | Schering Corp | Aromatic heterocyclic esters of steroids, their preparation and pharmaceutical compositions containing them |
| ZW6584A1 (en) | 1983-04-18 | 1985-04-17 | Glaxo Group Ltd | Phenethanolamine derivatives |
| US4607028A (en) | 1983-08-18 | 1986-08-19 | Ciba-Geigy Corporation | Novel carboxylic acid esters |
| EP0179583A1 (en) | 1984-10-04 | 1986-04-30 | Merck & Co. Inc. | A system for enhancing the water dissolution rate and solubility of poorly soluble drugs |
| US4861765A (en) | 1985-06-26 | 1989-08-29 | Jouveinal | 21-alkyl-, cycloalkyl- or aryl-substituted thio steroids and pharmaceutical compositions containing them |
| ZA872389B (en) | 1987-04-02 | 1987-11-25 | Advanced Polymer Systems Inc | Composition and method for delivering a steroid active ingredient |
| US4964069A (en) | 1987-05-12 | 1990-10-16 | International Business Machines Corporation | Self adjusting video interface |
| WO1989003390A1 (en) | 1987-10-13 | 1989-04-20 | Bodor Nicholas S | Soft steroids having anti-inflammatory activity |
| US4994439A (en) | 1989-01-19 | 1991-02-19 | California Biotechnology Inc. | Transmembrane formulations for drug administration |
| US5202316A (en) * | 1989-03-22 | 1993-04-13 | Roussel Uclaf | N,N,N',N'-6-(1-piperazinyl)-2,5-pyridinediamines |
| FR2644788B1 (fr) | 1989-03-22 | 1995-02-03 | Roussel Uclaf | Nouveaux steroides 3-ceto comportant une chaine en 17 amino-substituee, leur procede de preparation et les intermediaires de ce procede, leur application comme medicaments et les compositions pharmaceutiques les contenant |
| JPH07116215B2 (ja) | 1989-04-19 | 1995-12-13 | エスエス製薬株式会社 | 新規なステロイド化合物 |
| JPH04506066A (ja) | 1989-06-16 | 1992-10-22 | ジ・アップジョン・カンパニー | 脈管形成を抑制するためのスラミン・タイプの化合物および脈管形成抑止ステロイド類 |
| IL95590A (en) | 1989-09-08 | 1996-06-18 | Glaxo Group Ltd | Medicinal preparations containing Salmetrol and Pluticasone Propionate |
| DE3931041C2 (de) | 1989-09-16 | 2000-04-06 | Boehringer Ingelheim Kg | Ester von Thienylcarbonsäuren mit Aminoalkoholen, ihre Quaternierungsprodukte, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| DE4025342A1 (de) * | 1990-08-10 | 1992-02-13 | Hoechst Ag | In 17-stellung substituierte corticoid-17-alkylcarbonate, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| JP3087763B2 (ja) | 1990-11-30 | 2000-09-11 | 三井化学株式会社 | 新規な複素環式化合物およびそれを含有する医薬組成物 |
| ES2187500T3 (es) | 1991-02-21 | 2003-06-16 | Smithkline Beecham Corp | Uso de topotecano en el tratamiento del carcinoma pulmonar no de celulas pequeñas. |
| GB9103764D0 (en) | 1991-02-22 | 1991-04-10 | Glaxo Group Ltd | Compositions |
| US5250293A (en) | 1991-04-22 | 1993-10-05 | Gleich Gerald J | Method for the treatment of hypersensitivity diseases by administration of anionic polymers |
| TW247878B (enExample) | 1991-07-02 | 1995-05-21 | Takeda Pharm Industry Co Ltd | |
| US6127353A (en) | 1991-09-06 | 2000-10-03 | Schering Corporation | Mometasone furoate monohydrate, process for making same and pharmaceutical compositions |
| US5658549A (en) | 1991-12-12 | 1997-08-19 | Glaxo Group Limited | Aerosol formulations containing propellant 134a and fluticasone propionate |
| NZ263686A (en) | 1993-03-17 | 1997-09-22 | Minnesota Mining & Mfg | Medicinal aerosol with dispersing aid derived from a hydroxy acid, an amino acid and/or a mercapto acid |
| DE4328819A1 (de) | 1993-08-27 | 1995-03-02 | Hoechst Ag | Corticosteroid-17-alkylcarbonat-21/0/-Carbonsäure- und Kohlensäureester, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| DE4333920A1 (de) * | 1993-10-05 | 1995-04-13 | Hoechst Ag | Corticoid-17,21-dicarbonsäureester sowie Corticosteroid-17-carbonsäureester-21-kohlensäureester, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| US5420120A (en) | 1993-12-17 | 1995-05-30 | Alcon Laboratories, Inc. | Anti-inflammatory glucocorticoid compounds for topical ophthalmic use |
| US5837699A (en) | 1994-01-27 | 1998-11-17 | Schering Corporation | Use of mometasone furoate for treating upper airway passage diseases |
| IL109656A (en) | 1994-05-15 | 1998-02-22 | Chemagis Ltd | Process for the manufacture of androstane - 17 - carbothioates and androstane - 17 - carbothioates prepared thereby |
| GB9410222D0 (en) | 1994-05-21 | 1994-07-06 | Glaxo Wellcome Australia Ltd | Medicaments |
| GB9419536D0 (en) | 1994-09-28 | 1994-11-16 | Glaxo Inc | Medicaments |
| SA95160463B1 (ar) | 1994-12-22 | 2005-10-04 | استرا أكتيبولاج | مساحيق للاستنشاق |
| JPH08291072A (ja) | 1995-04-22 | 1996-11-05 | Kissei Pharmaceut Co Ltd | 吸入用粉末製剤用結晶とその製造方法 |
| JPH08291073A (ja) | 1995-04-22 | 1996-11-05 | Kissei Pharmaceut Co Ltd | 医薬品組成物及びその製造方法 |
| DE19528145A1 (de) | 1995-08-01 | 1997-02-06 | Boehringer Ingelheim Kg | Neue Arzneimittel und ihre Verwendung |
| GB9521696D0 (en) | 1995-10-23 | 1996-01-03 | Bayer Ag | Combination of LTD4 receptor antagonists with glucocorticosteriods |
| US5766620A (en) | 1995-10-23 | 1998-06-16 | Theratech, Inc. | Buccal delivery of glucagon-like insulinotropic peptides |
| US5792758A (en) | 1995-12-08 | 1998-08-11 | G. D. Searle & Co. | Steroid nitrite ester derivatives useful as anti-inflammatory drugs |
| US5707984A (en) | 1995-12-08 | 1998-01-13 | G. D. Searle & Co. | Steroid nitrite/nitrate ester derivatives useful as anti-inflammatory drugs |
| NZ324373A (en) | 1995-12-29 | 1999-10-28 | Glaxo Group Ltd | Lactone derivatives of 17-beta-carboxy, carbonyl-thio and amide androstane derivatives |
| US5985862A (en) | 1996-05-02 | 1999-11-16 | G.D. Searle & Co. | Pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs |
| US5981517A (en) | 1996-05-09 | 1999-11-09 | Soft Drugs, Inc. | Androstene derivatives |
| CA2256721A1 (en) | 1996-06-04 | 1997-12-11 | The Procter & Gamble Company | A nasal spray containing an intranasal steroid and an antihistamine |
| GB9622173D0 (en) | 1996-10-24 | 1996-12-18 | Glaxo Group Ltd | Particulate Products |
| US5919776A (en) | 1996-12-20 | 1999-07-06 | Merck & Co., Inc. | Substituted aminoquinolines as modulators of chemokine receptor activity |
| WO1998034598A2 (en) | 1997-02-07 | 1998-08-13 | Gist-Brocades B.V. | Homogeneous granulated formulations for dose sipping technology |
| US6126919A (en) | 1997-02-07 | 2000-10-03 | 3M Innovative Properties Company | Biocompatible compounds for pharmaceutical drug delivery systems |
| EP1003501B9 (en) | 1997-04-02 | 2005-06-08 | The Brigham And Women's Hospital, Inc. | Use of an agent for lowering the risk of cardiovascular disease |
| AU8439998A (en) | 1997-06-30 | 1999-01-25 | Glaxo Group Limited | Compounds |
| SE9704186D0 (sv) | 1997-11-14 | 1997-11-14 | Astra Ab | New composition of matter |
| SE9704833D0 (sv) | 1997-12-22 | 1997-12-22 | Astra Ab | New formulation |
| US5972920A (en) | 1998-02-12 | 1999-10-26 | Dermalogix Partners, Inc. | Formulation containing a carrier, active ingredient, and surfactant for treating skin disorders |
| US6506766B1 (en) | 1998-02-13 | 2003-01-14 | Abbott Laboratories | Glucocortiocoid-selective antinflammatory agents |
| US6136294C1 (en) | 1998-09-22 | 2002-09-24 | Aeropharm Technology Inc | Amino acid stabilized medical aerosol formulation |
| US6458338B1 (en) * | 1998-09-22 | 2002-10-01 | Aeropharm Technology Incorporated | Amino acid stabilized medicinal aerosol formulations |
| US6261539B1 (en) | 1998-12-10 | 2001-07-17 | Akwete Adjei | Medicinal aerosol formulation |
| EP1055223B1 (en) * | 1998-12-17 | 2011-07-13 | Sony Computer Entertainment Inc. | Apparatus and method for generating music data |
| GB9828721D0 (en) | 1998-12-24 | 1999-02-17 | Glaxo Group Ltd | Novel apparatus and process |
| AU3703900A (en) | 1999-02-24 | 2000-09-14 | Nitromed, Inc. | Nitrosated and nitrosylated steroids for the treatment of cardiovascular diseases and disorders |
| AU3411000A (en) | 1999-03-24 | 2000-10-09 | Glenayre Electronics, Inc | Computation and quantization of voiced excitation pulse shapes in linear predictive coding of speech |
| HUP0201243A3 (en) | 1999-04-30 | 2002-11-28 | Pfizer Prod Inc | Glucocorticoid receptor modulators, pharmaceutical compositions containing them and their use |
| US6395300B1 (en) | 1999-05-27 | 2002-05-28 | Acusphere, Inc. | Porous drug matrices and methods of manufacture thereof |
| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| GB9918559D0 (en) * | 1999-08-07 | 1999-10-06 | Glaxo Wellcome Kk | Novel pharmaceutical formulation |
| US20020081266A1 (en) * | 1999-08-20 | 2002-06-27 | Norton Healthcare Ltd. | Spray dried powders for pulmonary or nasal administration |
| WO2001015744A1 (en) | 1999-08-31 | 2001-03-08 | The Brigham And Women's Hospital, Inc. | Systemic inflammatory markers as diagnostic tools in the prevention of atherosclerotic diseases |
| AU7703400A (en) | 1999-09-14 | 2001-04-17 | Xenoport, Inc. | Substrates and screening methods for transport proteins |
| US6596261B1 (en) | 2000-01-25 | 2003-07-22 | Aeropharm Technology Incorporated | Method of administering a medicinal aerosol formulation |
| JP2004501067A (ja) | 2000-01-28 | 2004-01-15 | ローム アンド ハース カンパニー | 高められた特性をもつ医薬 |
| US20020133032A1 (en) | 2000-02-25 | 2002-09-19 | Jufang Barkalow | Method for the preparation of fluticasone and related 17beta-carbothioic esters using a novel carbothioic acid synthesis and novel purification methods |
| GB0009583D0 (en) | 2000-04-18 | 2000-06-07 | Glaxo Group Ltd | Respiratory formulations |
| GB0009606D0 (en) | 2000-04-18 | 2000-06-07 | Glaxo Group Ltd | Therapeutic combinations |
| GB0009591D0 (en) | 2000-04-18 | 2000-06-07 | Glaxo Group Ltd | Medical combinations |
| GB0009592D0 (en) | 2000-04-18 | 2000-06-07 | Glaxo Group Ltd | Respiratory combinations |
| GB0015876D0 (en) | 2000-06-28 | 2000-08-23 | Novartis Ag | Organic compounds |
| GB0016040D0 (en) | 2000-06-29 | 2000-08-23 | Glaxo Group Ltd | Novel process for preparing crystalline particles |
| GB0017988D0 (en) | 2000-07-21 | 2000-09-13 | Glaxo Group Ltd | Novel process |
| US20020037877A1 (en) | 2000-07-26 | 2002-03-28 | Alcon Universal Ltd. | Pharmaceutical suspension compositions lacking a polymeric suspending agent |
| SI1305329T2 (sl) | 2000-08-05 | 2015-07-31 | Glaxo Group Limited | S-fluorometil ester 6alfa,9alfa-difluoro-17alfa-(2-furanilkarboksil)oksi-11beta-hidroksi- 16alfa-metil-3-okso-androst-1,4-dien-17-karbotiojske kisline kot protivnetno sredstvo |
| US6787532B2 (en) * | 2000-08-05 | 2004-09-07 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivatives |
| US6777399B2 (en) * | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
| US6777400B2 (en) * | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6858593B2 (en) * | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| AR032362A1 (es) | 2000-08-14 | 2003-11-05 | Glaxo Group Ltd | Formulacion topica estable de una emulsion de aceite en agua y proceso para su preparacion |
| NZ525055A (en) | 2000-09-29 | 2004-09-24 | Glaxo Group Ltd | Compounds useful in the treatment of inflammatory diseases |
| AU2002210575A1 (en) | 2000-10-31 | 2002-05-15 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Novel medicament compositions based on anticholinergics and corticosteroids |
| DE10062712A1 (de) | 2000-12-15 | 2002-06-20 | Boehringer Ingelheim Pharma | Neue Arzneimittelkompositionen auf der Basis von Anticholinergika und Corticosteroiden |
| CN101518537A (zh) | 2000-12-22 | 2009-09-02 | 日本新药株式会社 | 炎症性呼吸道疾病的预防/治疗剂 |
| US20020132803A1 (en) | 2001-01-05 | 2002-09-19 | Mahendra Dedhiya | Fluticasone suspension formulation, spray pattern method, and nasal spray apparatus |
| GB0103630D0 (en) | 2001-02-14 | 2001-03-28 | Glaxo Group Ltd | Chemical compounds |
| US7144908B2 (en) | 2001-03-08 | 2006-12-05 | Glaxo Group Limited | Agonists of beta-adrenoceptors |
| US7045658B2 (en) | 2001-03-22 | 2006-05-16 | Glaxo Group Limited | Formailide derivatives as beta2-adrenoreceptor agonists |
| UA77656C2 (en) | 2001-04-07 | 2007-01-15 | Glaxo Group Ltd | S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent |
| US20050070487A1 (en) | 2001-04-24 | 2005-03-31 | Nyce Jonathan W. | Composition, formulations and kit for treatment of respiratory and lung disease with non-glucocorticoid steroids and/or ubiquinone and a bronchodilating agent |
| CA2445839A1 (en) | 2001-04-30 | 2002-11-07 | Glaxo Group Limited | Anti-inflammatory 17.beta.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.alpha |
| JP2005500290A (ja) | 2001-06-12 | 2005-01-06 | グラクソ グループ リミテッド | 抗炎症性の、１７β−カルボチオアートアンドロスタン誘導体である１７α複素環エステル |
| US20030018019A1 (en) * | 2001-06-23 | 2003-01-23 | Boehringer Ingelheim Pharma Kg | Pharmaceutical compositions based on anticholinergics, corticosteroids and betamimetics |
| AU2002321884A1 (en) | 2001-08-03 | 2003-02-24 | Smithkline Beecham Corporation | A method for preparing fluticasone derivatives |
| GB0124523D0 (en) | 2001-10-12 | 2001-12-05 | Glaxo Group Ltd | Pharmaceutical combination |
| GB0125259D0 (en) | 2001-10-20 | 2001-12-12 | Glaxo Group Ltd | Novel compounds |
| US7399743B2 (en) | 2001-10-26 | 2008-07-15 | The Scripps Research Institute | Targeted thrombosis |
| KR20040068544A (ko) | 2001-11-05 | 2004-07-31 | 더 브리검 앤드 우먼즈 하스피털, 인크. | 아테롬성 동맥경화증의 예후 표지로서의 가용성 ｃｄ40ｌ(ｃｄ154) |
| GB0127160D0 (en) | 2001-11-12 | 2002-01-02 | Glaxo Group Ltd | Novel compounds |
| WO2003042229A1 (en) | 2001-11-12 | 2003-05-22 | Glaxo Group Limited | Non-aromatic heterocyclic esters of furan-2-one-esters of 17.beta.-carboxyl or 17.beta.-carbothio glucocorticoids |
| AU2002356759A1 (en) | 2001-12-01 | 2003-06-17 | Glaxo Group Limited | 17.alpha. -cyclic esters of 16-methylpregnan-3,20-dione as anti-inflammatory agents |
| WO2003072592A1 (en) | 2002-01-15 | 2003-09-04 | Glaxo Group Limited | 17.alpha-cycloalkyl/cycloylkenyl esters of alkyl-or haloalkyl-androst-4-en-3-on-11.beta.,17.alpha.-diol 17.beta.-carboxylates as anti-inflammatory agents |
| AU2003201693A1 (en) | 2002-01-21 | 2003-09-02 | Glaxo Group Limited | Non-aromatic 17.alpha.-esters of androstane-17.beta.-carboxylate esters as anti-inflammatory agents |
| GB0202216D0 (en) | 2002-01-31 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| DE10216429A1 (de) | 2002-04-12 | 2003-10-23 | Boehringer Ingelheim Pharma | Arzneimittel enthaltend Steroide und ein neues Anticholinergikum |
| JP3691459B2 (ja) | 2002-06-14 | 2005-09-07 | 久光メディカル株式会社 | 粉末状吸入剤組成物 |
| GB0217504D0 (en) | 2002-07-29 | 2002-09-04 | Novartis Ag | Organic compounds |
| US7244742B2 (en) * | 2002-08-17 | 2007-07-17 | Boehringer Ingelheim Pharma Gmbh & Co Kg | Pharmaceutical compositions for inhalation containing an anticholinergic, corticosteroid and betamimetic |
-
2002
- 2002-02-04 US US10/067,020 patent/US6858596B2/en not_active Expired - Lifetime
-
2003
- 2003-02-04 ES ES03737365T patent/ES2699507T3/es not_active Expired - Lifetime
- 2003-02-04 EP EP18193195.7A patent/EP3510994A1/en not_active Withdrawn
- 2003-02-04 JP JP2003565449A patent/JP4838493B2/ja not_active Expired - Lifetime
- 2003-02-04 AU AU2003244506A patent/AU2003244506A1/en not_active Abandoned
- 2003-02-04 US US10/502,902 patent/US20050164996A1/en not_active Abandoned
- 2003-02-04 EP EP03737365.1A patent/EP1478340B1/en not_active Expired - Lifetime
- 2003-02-04 WO PCT/GB2003/000504 patent/WO2003066024A1/en not_active Ceased
-
2004
- 2004-08-13 US US10/918,779 patent/US7541350B2/en not_active Expired - Lifetime
-
2010
- 2010-08-18 US US12/858,940 patent/US20100311706A1/en not_active Abandoned
-
2012
- 2012-02-10 US US13/370,493 patent/US20120142651A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003066024A1 (en) | 2003-08-14 |
| US20120142651A1 (en) | 2012-06-07 |
| US20050020549A1 (en) | 2005-01-27 |
| EP1478340A1 (en) | 2004-11-24 |
| JP4838493B2 (ja) | 2011-12-14 |
| US20020165211A1 (en) | 2002-11-07 |
| EP1478340B1 (en) | 2018-09-12 |
| EP3510994A1 (en) | 2019-07-17 |
| JP2005521673A (ja) | 2005-07-21 |
| US7541350B2 (en) | 2009-06-02 |
| US20050164996A1 (en) | 2005-07-28 |
| US6858596B2 (en) | 2005-02-22 |
| AU2003244506A1 (en) | 2003-09-02 |
| US20100311706A1 (en) | 2010-12-09 |
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