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GB1384372A - Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids - Google Patents

Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids

Info

Publication number
GB1384372A
GB1384372A GB278771A GB278771A GB1384372A GB 1384372 A GB1384372 A GB 1384372A GB 278771 A GB278771 A GB 278771A GB 278771 A GB278771 A GB 278771A GB 1384372 A GB1384372 A GB 1384372A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
alkyl
ene
novel
products
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
Application number
GB278771A
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 Laboratories Ltd
Original Assignee
Glaxo Laboratories 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
Application filed by Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Priority to GB278771A priority Critical patent/GB1384372A/en
Priority to NO111/72A priority patent/NO137321C/en
Priority to IL38589A priority patent/IL38589A/en
Priority to JP735572A priority patent/JPS5611720B1/ja
Priority to BE778285A priority patent/BE778285A/en
Priority to DK29672*#A priority patent/DK132894C/en
Priority to CH84372A priority patent/CH602786A5/xx
Priority to ES399057A priority patent/ES399057A1/en
Priority to NLAANVRAGE7200818,A priority patent/NL172511C/en
Priority to CA132,814A priority patent/CA1003820A/en
Priority to ZA720401A priority patent/ZA72401B/en
Priority to IE82/72A priority patent/IE36000B1/en
Priority to AU38110/72A priority patent/AU473868B2/en
Priority to FR7201852A priority patent/FR2122539B1/fr
Priority to SE7200662A priority patent/SE383522B/en
Priority to DE19722202691 priority patent/DE2202691A1/en
Publication of GB1384372A publication Critical patent/GB1384372A/en
Priority to HK342/78A priority patent/HK34278A/en
Priority to MY308/78A priority patent/MY7800308A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
    • C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1384372 Derivatives of 17α-hydroxy-androst- 4 - ene - 17# - carboxylic acid GLAXO LABORATORIES Ltd 20 Jan 1972 [20 Jan 1971] 2787/71 Heading C2U [Also in Division A5] Novel steroids of the formulµ wherein (a) X is H, Cl or F; R 1 is #-OH or, when X is Cl, R 1 may also be #-Cl; R 2 is H, =CH 2 or α- or #-CH 3 ; R 3 is H, C 1-3 alkyl or phenyl; R 4 is C 1-4 alkyl optionally substituted by either at least one halogen or by C 2-5 alkoxycarbonyl, or is (C 2-5 alkanoyloxy)-(C 2-4 alkyl) and the #<SP>1</SP>- double bond is optional; or (b) X is Cl or F; R 1 is = O ; R 3 is CH 3 or C 2 H 5 ; and R 2 , R 4 and the #<SP>1</SP>-double bond are as defined above, but excluding the n- and iso-propyl and n-butyl esters of 17α - formyloxy - 11# - hydroxy - 3 - ketoandrost - 4 - ene - 17# - carboxylic acid and also excluding the C 1-4 alkyl esters of 11#,17α- dihydroxy - 3 - keto - androst - 4 - ene - 17#- carboxylic acid, and the novel anhydrides (including mixed anhydrides) of the free 17#- carboxylic acids, and the novel 2<SP>1</SP>-hydroxyethyl 9α - fluoro - 11# - hydroxy - 16# - methyl - 3- oxo - 17α - propionyloxy - androsta - 1,4 - diene- 17#-carboxylate, are prepared from the corresponding 17α - hydroxy - 17# - carboxy - steroids by standard esterification and acylation procedures. Resulting 11#-ols may be oxidized to 11-ones and 17-acylates may be hydrolysed to 17α-ols and subsequently re-esterified. Acylation of the free 17α-OH-17#-CO 2 H compounds with carboxylic acid anhydrides results in the formation of 17α-esters of the mixed anhydrides which are then subjected to solvolysis to give the free 17#-CO 2 H compounds. Substituents in the alkyl group R 4 may be interconverted by standard procedures or formed from other substituents, e.g. a hydroxyalkyl ester may be prepared, then converted via a sulphonyloxy ester to a halo-alkyl ester or, alternatively, O- acylated. Products wherein R 4 contains an α-halogen atom may be obtained by reacting the 17#- CO 2 H compound with an aldehyde and a hydrohalic acid. #<SP>1,4</SP>-products may be partially reduced to #<SP>4</SP>-products. 17α - Hydroxy - 17# - carboxy - steroid starting materials are prepared by oxidation of pregnanes containing a 17#-COCH 2 OH side chain. This reaction may also be effected on 17α-acyloxy starting materials, giving 17α-acyloxy products. The novel 17α-acyloxy-17#-(esterified carboxy)-steroids of the above formula are antiinflammatory agents and may be incorporated in pharmaceutical compositions (see Heading A5B).
GB278771A 1971-01-20 1971-01-20 Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids Expired GB1384372A (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
GB278771A GB1384372A (en) 1971-01-20 1971-01-20 Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids
NO111/72A NO137321C (en) 1971-01-20 1972-01-19 ANALOGICAL PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE 3-OXO-17ALFA-ACYLOXYANDROST-4-EN-17BETA-CARBOXYLIC ACID ESTERS
IL38589A IL38589A (en) 1971-01-20 1972-01-19 11beta-hydroxy-17alpha-acyloxy-3-oxo-androst-4-ene-17beta-carboxylic acid esters
CA132,814A CA1003820A (en) 1971-01-20 1972-01-20 Steroid compounds
AU38110/72A AU473868B2 (en) 1971-01-20 1972-01-20 Steroid compounds
DK29672*#A DK132894C (en) 1971-01-20 1972-01-20 ANALOGICAL PROCEDURE FOR THE PRODUCTION OF 3-OXO-17ALFA-ACYLOXYANDROST-4-EN-17BETA-CARBOXYLIC ACID RESIDENTS
CH84372A CH602786A5 (en) 1971-01-20 1972-01-20
ES399057A ES399057A1 (en) 1971-01-20 1972-01-20 Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids
NLAANVRAGE7200818,A NL172511C (en) 1971-01-20 1972-01-20 METHOD FOR PREPARING OR MANUFACTURING A MEDICINE AGAINST INFLAMMATION
JP735572A JPS5611720B1 (en) 1971-01-20 1972-01-20
ZA720401A ZA72401B (en) 1971-01-20 1972-01-20 Steroid compounds
IE82/72A IE36000B1 (en) 1971-01-20 1972-01-20 Derivatives of 17alpha-hydroxy-androst-4-ene-17beta-carboxylic acids
BE778285A BE778285A (en) 1971-01-20 1972-01-20 STEROID COMPOUNDS WITH ANTI-PHLOGISTIC ACTIVITY
FR7201852A FR2122539B1 (en) 1971-01-20 1972-01-20
SE7200662A SE383522B (en) 1971-01-20 1972-01-20 PROCEDURE FOR THE PREPARATION OF ANTI-INFLAMMATORY EFFICIENT 17-CARBOXYLATE OF STEROIDS BELONGING TO THE ANDROSTAN SERIES.
DE19722202691 DE2202691A1 (en) 1971-01-20 1972-01-20 Steroid compounds
HK342/78A HK34278A (en) 1971-01-20 1978-06-29 Derivatives of 17alpha-hydroxy-androst-4ene-17beta-carboxylic acids
MY308/78A MY7800308A (en) 1971-01-20 1978-12-30 Derivatives of 17(alpha)-hydroxy-androst-4-ene-17(beta)-carboxylic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB278771A GB1384372A (en) 1971-01-20 1971-01-20 Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids

Publications (1)

Publication Number Publication Date
GB1384372A true GB1384372A (en) 1975-02-19

Family

ID=9745890

Family Applications (1)

Application Number Title Priority Date Filing Date
GB278771A Expired GB1384372A (en) 1971-01-20 1971-01-20 Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids

Country Status (17)

Country Link
JP (1) JPS5611720B1 (en)
AU (1) AU473868B2 (en)
BE (1) BE778285A (en)
CA (1) CA1003820A (en)
CH (1) CH602786A5 (en)
DE (1) DE2202691A1 (en)
DK (1) DK132894C (en)
ES (1) ES399057A1 (en)
FR (1) FR2122539B1 (en)
GB (1) GB1384372A (en)
HK (1) HK34278A (en)
IE (1) IE36000B1 (en)
IL (1) IL38589A (en)
NL (1) NL172511C (en)
NO (1) NO137321C (en)
SE (1) SE383522B (en)
ZA (1) ZA72401B (en)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2422688A1 (en) * 1978-02-08 1979-11-09 Glaxo Group Ltd ANDROSTANE SERIES ANTIPHLOGISTIC STEROID
US5981517A (en) * 1996-05-09 1999-11-09 Soft Drugs, Inc. Androstene derivatives
WO2002000679A3 (en) * 2000-06-28 2002-03-28 Novartis Ag 9.alpha.-chloro-6.alpha.-fluoro-17.alpha.-hydroxy-16-methyl-17-beta-methoxycarbonyl-androst-1,4-dienes esterified in position 17.alpha. by a cyclic acyl group
US6750210B2 (en) 2000-08-05 2004-06-15 Smithkline Beecham Corporation Formulation containing novel anti-inflammatory androstane derivative
US6759398B2 (en) 2000-08-05 2004-07-06 Smithkline Beecham Corporation Anti-inflammatory androstane derivative
US6777400B2 (en) 2000-08-05 2004-08-17 Smithkline Beecham Corporation Anti-inflammatory androstane derivative compositions
US6777399B2 (en) 2000-08-05 2004-08-17 Smithkline Beecham Corporation Anti-inflammatory androstane derivative compositions
US6787532B2 (en) 2000-08-05 2004-09-07 Smithkline Beecham Corporation Formulation containing anti-inflammatory androstane derivatives
WO2005005451A1 (en) 2003-07-11 2005-01-20 Glaxo Group Limited Specific glucocorticosteroid compound having anti- inflammatory activity
US6858593B2 (en) 2000-08-05 2005-02-22 Smithkline Beecham Corporation Anti-inflammatory androstane derivative compositions
US6858596B2 (en) 2000-08-05 2005-02-22 Smithkline Beecham Corporation Formulation containing anti-inflammatory androstane derivative
US6878698B2 (en) 2001-04-07 2005-04-12 Glaxo Group Limited Anti-inflammatory androstane derivatives
US7125985B2 (en) 2000-08-05 2006-10-24 Glaxo Group Limited Compounds useful in the manufacture of an anti-inflammatory androstane derivative
US7291608B2 (en) 2001-04-30 2007-11-06 Glaxo Group Limited Anti-inflammatory 17.β.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.α
US7419971B2 (en) 2003-06-19 2008-09-02 Bodor Nicholas S Enhancement of activity and/or duration of action of selected anti-inflammatory steroids for topical or other local application
US7498321B2 (en) 2000-08-05 2009-03-03 Glaxo Group Limited 17β-carbothioate 17α-arylcarbonyloxyloxy androstane derivative as anti-inflammatory agents
US7560448B2 (en) 2003-06-19 2009-07-14 Bodor Nicholas S Enhancement of activity and/or duration of action of soft anti-inflammatory steroids for topical or other local application
US7579335B2 (en) 2005-01-10 2009-08-25 Glaxo Group Limited Androstane 17α-carbonate derivatives for use in the treatment of allergic and inflammatory conditions
US7687484B2 (en) 2006-05-25 2010-03-30 Bodor Nicholas S Transporter enhanced corticosteroid activity
US7691811B2 (en) 2006-05-25 2010-04-06 Bodor Nicholas S Transporter-enhanced corticosteroid activity and methods and compositions for treating dry eye
US8163723B2 (en) 2002-06-14 2012-04-24 Cipla Limited Combination of azelastine and steroids
US8835410B2 (en) 2011-05-10 2014-09-16 Bodor Laboratories, Inc. Treatment of eyelid dermatitis

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1438940A (en) * 1972-07-19 1976-06-09 Glaxo Lab Ltd 17beta-haloalkoxycarbonyl-17alpha-oxysteroids
DE2365102C2 (en) * 1973-12-21 1982-12-02 Schering Ag, 1000 Berlin Und 4619 Bergkamen New pregnanic acid derivatives
DE2444618C2 (en) * 1974-09-16 1984-01-19 Schering AG, 1000 Berlin und 4709 Bergkamen New Pregnan-21-Acid-Derivatives
DE2319479C2 (en) * 1973-04-14 1982-10-28 Schering Ag, 1000 Berlin Und 4619 Bergkamen Pregnanic acid derivatives, processes for their production and pharmaceutical preparations containing them
GB1514476A (en) * 1974-08-30 1978-06-14 Glaxo Lab Ltd Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates
SE427276B (en) * 1975-04-03 1983-03-21 Hoffmann La Roche PROCEDURE FOR PREPARING D-HOMOSTEROIDS
CH628355A5 (en) * 1976-02-24 1982-02-26 Ciba Geigy Ag METHOD FOR PRODUCING NEW ANDROSTADIEN-17BETA-CARBONIC ACIDS AND THEIR ESTERS AND SALTS.
CA1138857A (en) * 1979-01-24 1983-01-04 Leo Alig D-homosteroids
SE449106B (en) * 1980-07-10 1987-04-06 Otsuka Pharma Co Ltd STEROID WITH ANTI-INFLAMMATORY EFFECT AND COMPOSITION CONTAINING THIS
JPS59139315A (en) * 1983-01-31 1984-08-10 Taisho Pharmaceut Co Ltd Cream agent
US4607028A (en) * 1983-08-18 1986-08-19 Ciba-Geigy Corporation Novel carboxylic acid esters
DE102010029877A1 (en) 2010-06-09 2011-12-15 Bayer Schering Pharma Aktiengesellschaft Preparing 1,4-pregna-dienoic acid derivative from 20-hydroxysteroid derivative by Swern oxidation, comprises adding 20-hydroxysteroid derivative in mixture of e.g. secondary amine and dimethylsulfoxide, and adding chlorosulfonic acid
DE102010029875A1 (en) 2010-06-09 2011-12-15 Bayer Schering Pharma Aktiengesellschaft Preparing 1,4-pregna-dienoic acid derivatives, comprises oxidizing 20-oxo-steroid derivatives to 20-hydroxysteroid derivatives in the presence of copper(II) salts with hydroxyalkyl, and oxidizing the 20-oxo-steroid derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3636010A (en) * 1968-12-23 1972-01-18 Ciba Geigy Corp Esters of steroid-17-carboxylic acids

Cited By (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2422688A1 (en) * 1978-02-08 1979-11-09 Glaxo Group Ltd ANDROSTANE SERIES ANTIPHLOGISTIC STEROID
US5981517A (en) * 1996-05-09 1999-11-09 Soft Drugs, Inc. Androstene derivatives
US6921757B2 (en) 2000-06-28 2005-07-26 Novartis Ag Organic compounds
CZ302513B6 (en) * 2000-06-28 2011-06-29 Novartis Ag Steroid, pharmaceutical composition in which the steroid is comprised, process for preparing such steroid and intermediates for the preparation process
WO2002000679A3 (en) * 2000-06-28 2002-03-28 Novartis Ag 9.alpha.-chloro-6.alpha.-fluoro-17.alpha.-hydroxy-16-methyl-17-beta-methoxycarbonyl-androst-1,4-dienes esterified in position 17.alpha. by a cyclic acyl group
US6787532B2 (en) 2000-08-05 2004-09-07 Smithkline Beecham Corporation Formulation containing anti-inflammatory androstane derivatives
US7498321B2 (en) 2000-08-05 2009-03-03 Glaxo Group Limited 17β-carbothioate 17α-arylcarbonyloxyloxy androstane derivative as anti-inflammatory agents
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
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
US6777399B2 (en) 2000-08-05 2004-08-17 Smithkline Beecham Corporation Anti-inflammatory androstane derivative compositions
US7125985B2 (en) 2000-08-05 2006-10-24 Glaxo Group Limited Compounds useful in the manufacture of an anti-inflammatory androstane derivative
US7132532B2 (en) 2000-08-05 2006-11-07 Glaxo Group Limited Compounds useful in the manufacture of an anti-inflammatory androstane derivative
US7144845B2 (en) 2000-08-05 2006-12-05 Glaxo Group Limited Compounds useful in the manufacture of an anti-inflammatory androstane derivative
US7629335B2 (en) 2000-08-05 2009-12-08 Glaxo Group Limited Anti-inflammatory androstane derivative
US7541350B2 (en) 2000-08-05 2009-06-02 Glaxo Group Limited Formulation containing anti-inflammatory androstane derivative
US7531528B2 (en) 2000-08-05 2009-05-12 Glaxo Group Limited Formulation containing anti-inflammatory androstane derivatives
US6878698B2 (en) 2001-04-07 2005-04-12 Glaxo Group Limited Anti-inflammatory androstane derivatives
US7291608B2 (en) 2001-04-30 2007-11-06 Glaxo Group Limited Anti-inflammatory 17.β.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.α
US7592329B2 (en) 2002-02-04 2009-09-22 Glaxo Group Limited Crystalline complexes of fluticasone-2-furoate
US8318709B2 (en) 2002-06-14 2012-11-27 Cipla Limited Combination of azelastine and mometasone for nasal administration
US8163723B2 (en) 2002-06-14 2012-04-24 Cipla Limited Combination of azelastine and steroids
US9901585B2 (en) 2002-06-14 2018-02-27 Cipla Limited Combination of azelastine and fluticasone for nasal administration
US9259428B2 (en) 2002-06-14 2016-02-16 Cipla Limited Combination of azelastine and fluticasone for nasal administration
US8937057B2 (en) 2002-06-14 2015-01-20 Cipla Limited Combination of azelastine and mometasone for nasal administration
US8933060B2 (en) 2002-06-14 2015-01-13 Cipla Limited Combination of azelastine and ciclesonide for nasal administration
US8304405B2 (en) 2002-06-14 2012-11-06 Cipla Limited Combination of azelastine and ciclesonide for nasal administration
US8168620B2 (en) 2002-06-14 2012-05-01 Cipla Limited Combination of azelastine and steroids
US7419971B2 (en) 2003-06-19 2008-09-02 Bodor Nicholas S Enhancement of activity and/or duration of action of selected anti-inflammatory steroids for topical or other local application
US7776846B2 (en) 2003-06-19 2010-08-17 Bodor Nicholas S Enhancement of activity and/or duration of action of selected anti-inflammatory steroids for topical or other local application
US7560448B2 (en) 2003-06-19 2009-07-14 Bodor Nicholas S Enhancement of activity and/or duration of action of soft anti-inflammatory steroids for topical or other local application
US7923441B2 (en) 2003-06-19 2011-04-12 Bodor Nicholas S Enhancement of activity and/or duration of action of soft anti-inflammatory steroids for topical or other local application
AU2004255854B2 (en) * 2003-07-11 2009-10-22 Glaxo Group Limited Specific glucocorticosteroid compound having anti- inflammatory activity
US7638508B2 (en) 2003-07-11 2009-12-29 Glaxo Group Limited Glucocorticosteroid compound having anti-inflammatory activity
US7288536B2 (en) 2003-07-11 2007-10-30 Glaxo Group Limited Specific glucocorticosteroid compound having anti-inflammatory activity
WO2005005451A1 (en) 2003-07-11 2005-01-20 Glaxo Group Limited Specific glucocorticosteroid compound having anti- inflammatory activity
JP2009513533A (en) * 2003-07-11 2009-04-02 グラクソ グループ リミテッド Certain glucocorticosteroid compounds with anti-inflammatory activity
US7291609B2 (en) 2003-07-11 2007-11-06 Glaxo Group Limited Specific glucocorticosteroid compound having anti-inflammatory activity
US7579335B2 (en) 2005-01-10 2009-08-25 Glaxo Group Limited Androstane 17α-carbonate derivatives for use in the treatment of allergic and inflammatory conditions
US7687484B2 (en) 2006-05-25 2010-03-30 Bodor Nicholas S Transporter enhanced corticosteroid activity
US7691811B2 (en) 2006-05-25 2010-04-06 Bodor Nicholas S Transporter-enhanced corticosteroid activity and methods and compositions for treating dry eye
US8835410B2 (en) 2011-05-10 2014-09-16 Bodor Laboratories, Inc. Treatment of eyelid dermatitis

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Publication number Publication date
NO137321B (en) 1977-10-31
NL7200818A (en) 1972-07-24
JPS5611720B1 (en) 1981-03-16
IE36000B1 (en) 1976-07-21
IL38589A (en) 1976-06-30
DE2202691A1 (en) 1972-08-03
IL38589A0 (en) 1972-03-28
ES399057A1 (en) 1974-11-01
FR2122539B1 (en) 1975-11-28
NL172511C (en) 1983-09-16
FR2122539A1 (en) 1972-09-01
ZA72401B (en) 1973-09-26
AU3811072A (en) 1973-07-26
HK34278A (en) 1978-07-07
CH602786A5 (en) 1978-08-15
BE778285A (en) 1972-07-20
DK132894B (en) 1976-02-23
SE383522B (en) 1976-03-15
IE36000L (en) 1972-07-20
DK132894C (en) 1976-07-26
CA1003820A (en) 1977-01-18
AU473868B2 (en) 1976-07-08
NO137321C (en) 1978-02-08
NL172511B (en) 1983-04-18

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PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee