IE36000B1 - Derivatives of 17alpha-hydroxy-androst-4-ene-17beta-carboxylic acids - Google Patents

Derivatives of 17alpha-hydroxy-androst-4-ene-17beta-carboxylic acids

Info

Publication number
IE36000B1
IE36000B1 IE82/72A IE8272A IE36000B1 IE 36000 B1 IE36000 B1 IE 36000B1 IE 82/72 A IE82/72 A IE 82/72A IE 8272 A IE8272 A IE 8272A IE 36000 B1 IE36000 B1 IE 36000B1
Authority
IE
Ireland
Prior art keywords
hydroxy
alkyl
ene
novel
products
Prior art date
Application number
IE82/72A
Other versions
IE36000L (en
Original Assignee
Glaxo Lab 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 Lab Ltd filed Critical Glaxo Lab Ltd
Publication of IE36000L publication Critical patent/IE36000L/en
Publication of IE36000B1 publication Critical patent/IE36000B1/en

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
    • 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
    • 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

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). [GB1384372A]
IE82/72A 1971-01-20 1972-01-20 Derivatives of 17alpha-hydroxy-androst-4-ene-17beta-carboxylic acids IE36000B1 (en)

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 (2)

Publication Number Publication Date
IE36000L IE36000L (en) 1972-07-20
IE36000B1 true IE36000B1 (en) 1976-07-21

Family

ID=9745890

Family Applications (1)

Application Number Title Priority Date Filing Date
IE82/72A IE36000B1 (en) 1971-01-20 1972-01-20 Derivatives of 17alpha-hydroxy-androst-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)

Families Citing this family (35)

* 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
DE2444618C2 (en) * 1974-09-16 1984-01-19 Schering AG, 1000 Berlin und 4709 Bergkamen New Pregnan-21-Acid-Derivatives
DE2365102C2 (en) * 1973-12-21 1982-12-02 Schering Ag, 1000 Berlin Und 4619 Bergkamen New pregnanic 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.
IT1114534B (en) * 1978-02-08 1986-01-27 Glaxo Group Ltd ANTI-INFLAMMATORY STEROID OF THE ANDROSTANE SERIES COMPOSITIONS THAT CONTAIN IT AND PROCEDURE TO PRODUCE IT
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
US5981517A (en) * 1996-05-09 1999-11-09 Soft Drugs, Inc. Androstene derivatives
GB0015876D0 (en) 2000-06-28 2000-08-23 Novartis Ag Organic compounds
US6750210B2 (en) 2000-08-05 2004-06-15 Smithkline Beecham Corporation Formulation containing novel anti-inflammatory androstane derivative
AR032361A1 (en) 2000-08-05 2003-11-05 Glaxo Group Ltd DERIVATIVES OF ANDROSTAN AND SALTS AND SOLVATOS OF THE SAME, ITS USE FOR THE MANUFACTURE OF MEDICINES, PHARMACEUTICAL COMPOSITIONS THAT INCLUDE SUCH COMPOUNDS, PROCESS FOR THE PREPARATION OF SUCH COMPOUNDS, AND USEFUL INTERMEDIARIES IN THE PREPARATION OF SUCH COMPOUNDS
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
US6787532B2 (en) 2000-08-05 2004-09-07 Smithkline Beecham Corporation Formulation containing anti-inflammatory androstane derivatives
GB0019172D0 (en) 2000-08-05 2000-09-27 Glaxo Group Ltd Novel compounds
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
WO2002088167A1 (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
GB2389530B (en) 2002-06-14 2007-01-10 Cipla Ltd Pharmaceutical compositions
DE602004008083T2 (en) 2003-06-19 2008-04-24 Nicholas S. Gainsville Bodor REINFORCEMENT OF THE ACTIVITY AND / OR DURABILITY OF SELECTED INFLAMMATORY STEROIDS
DE602004025002D1 (en) 2003-06-19 2010-02-25 Nicholas S Bodor INCREASING THE ACTIVITY AND / OR THE EFFICIENCY OF SOFT STEROIDS WITH ANTI-INFLAMMATORY IMPACT FOR TOPICAL OR LOCAL ADMINISTRATION
GB0316290D0 (en) * 2003-07-11 2003-08-13 Glaxo Group Ltd Novel compounds
ATE517908T1 (en) 2005-01-10 2011-08-15 Glaxo Group Ltd ANDROSTAN-17-ALPHA-CARBONATE DERIVATIVES FOR USE IN THE TREATMENT OF ALLERGIC AND INFLAMMATORY CONDITIONS
US7691811B2 (en) 2006-05-25 2010-04-06 Bodor Nicholas S Transporter-enhanced corticosteroid activity and methods and compositions for treating dry eye
US7687484B2 (en) 2006-05-25 2010-03-30 Bodor Nicholas S Transporter enhanced corticosteroid activity
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
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
US8835410B2 (en) 2011-05-10 2014-09-16 Bodor Laboratories, Inc. Treatment of eyelid dermatitis

Family Cites Families (1)

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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

Also Published As

Publication number Publication date
ES399057A1 (en) 1974-11-01
FR2122539A1 (en) 1972-09-01
NL172511C (en) 1983-09-16
IL38589A0 (en) 1972-03-28
BE778285A (en) 1972-07-20
DK132894B (en) 1976-02-23
CH602786A5 (en) 1978-08-15
NL172511B (en) 1983-04-18
NL7200818A (en) 1972-07-24
AU3811072A (en) 1973-07-26
ZA72401B (en) 1973-09-26
NO137321C (en) 1978-02-08
NO137321B (en) 1977-10-31
FR2122539B1 (en) 1975-11-28
AU473868B2 (en) 1976-07-08
DE2202691A1 (en) 1972-08-03
DK132894C (en) 1976-07-26
IE36000L (en) 1972-07-20
JPS5611720B1 (en) 1981-03-16
IL38589A (en) 1976-06-30
CA1003820A (en) 1977-01-18
HK34278A (en) 1978-07-07
SE383522B (en) 1976-03-15
GB1384372A (en) 1975-02-19

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