IE36000L - DERIVATIVES OF 17 Ó-HYDROXY-ANDROST-4-ENE-17ß- CARBOXYLIC¹ACIDS - Google Patents
DERIVATIVES OF 17 Ó-HYDROXY-ANDROST-4-ENE-17ß- CARBOXYLIC¹ACIDSInfo
- Publication number
- IE36000L IE36000L IE720082A IE8272A IE36000L IE 36000 L IE36000 L IE 36000L IE 720082 A IE720082 A IE 720082A IE 8272 A IE8272 A IE 8272A IE 36000 L IE36000 L IE 36000L
- Authority
- IE
- Ireland
- Prior art keywords
- hydroxy
- alkyl
- novel
- products
- ene
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 230000010933 acylation Effects 0.000 abstract 2
- 238000005917 acylation reaction Methods 0.000 abstract 2
- -1 hydroxyalkyl ester Chemical class 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition 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
- 150000003128 pregnanes Chemical class 0.000 abstract 1
- 238000003797 solvolysis reaction Methods 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
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).
[GB1384372A]
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 true IE36000L (en) | 1972-07-20 |
| IE36000B1 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)
| 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. |
| 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 |
| 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 |
| SI1775305T1 (en) | 2000-08-05 | 2015-01-30 | Glaxo Group Limited | 6.Alpha.,9.alpha.-difluoro-17.alpha.-'(2-furanylcarboxyl) oxyĆ-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androst-1,4,-diene-17-carbothiotic acid s-fluoromethyl ester as an anti-inflammatory agent |
| US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
| US6858593B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6777399B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| GB0019172D0 (en) | 2000-08-05 | 2000-09-27 | Glaxo Group Ltd | Novel compounds |
| US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| US6787532B2 (en) | 2000-08-05 | 2004-09-07 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivatives |
| 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 |
| KR100831534B1 (en) | 2001-04-30 | 2008-05-22 | 글락소 그룹 리미티드 | 17.beta.-carbothioate ester derivatives of anti-inflammatory androstanes with cyclic ester groups in the alpha position |
| 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 |
| WO2005000317A1 (en) | 2003-06-19 | 2005-01-06 | Bodor Nicholas S | Enhancement of activity and/or duration of action of soft anti-inflammatory steroids for topical or other local application |
| GB0316290D0 (en) * | 2003-07-11 | 2003-08-13 | Glaxo Group Ltd | Novel compounds |
| EP1841780B1 (en) | 2005-01-10 | 2011-07-27 | Glaxo Group Limited | Androstane 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 |
| 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 |
| US8835410B2 (en) | 2011-05-10 | 2014-09-16 | Bodor Laboratories, Inc. | Treatment of eyelid dermatitis |
Family Cites Families (1)
| 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 |
-
1971
- 1971-01-20 GB GB278771A patent/GB1384372A/en not_active Expired
-
1972
- 1972-01-19 NO NO111/72A patent/NO137321C/en unknown
- 1972-01-19 IL IL38589A patent/IL38589A/en unknown
- 1972-01-20 FR FR7201852A patent/FR2122539B1/fr not_active Expired
- 1972-01-20 IE IE82/72A patent/IE36000B1/en unknown
- 1972-01-20 CH CH84372A patent/CH602786A5/xx not_active IP Right Cessation
- 1972-01-20 NL NLAANVRAGE7200818,A patent/NL172511C/en not_active IP Right Cessation
- 1972-01-20 DE DE19722202691 patent/DE2202691A1/en not_active Ceased
- 1972-01-20 ES ES399057A patent/ES399057A1/en not_active Expired
- 1972-01-20 BE BE778285A patent/BE778285A/en not_active IP Right Cessation
- 1972-01-20 DK DK29672*#A patent/DK132894C/en active
- 1972-01-20 AU AU38110/72A patent/AU473868B2/en not_active Expired
- 1972-01-20 JP JP735572A patent/JPS5611720B1/ja active Pending
- 1972-01-20 CA CA132,814A patent/CA1003820A/en not_active Expired
- 1972-01-20 ZA ZA720401A patent/ZA72401B/en unknown
- 1972-01-20 SE SE7200662A patent/SE383522B/en unknown
-
1978
- 1978-06-29 HK HK342/78A patent/HK34278A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5611720B1 (en) | 1981-03-16 |
| FR2122539B1 (en) | 1975-11-28 |
| DK132894C (en) | 1976-07-26 |
| IL38589A (en) | 1976-06-30 |
| NL172511C (en) | 1983-09-16 |
| CH602786A5 (en) | 1978-08-15 |
| DK132894B (en) | 1976-02-23 |
| IE36000B1 (en) | 1976-07-21 |
| NO137321C (en) | 1978-02-08 |
| GB1384372A (en) | 1975-02-19 |
| DE2202691A1 (en) | 1972-08-03 |
| ES399057A1 (en) | 1974-11-01 |
| CA1003820A (en) | 1977-01-18 |
| ZA72401B (en) | 1973-09-26 |
| AU473868B2 (en) | 1976-07-08 |
| SE383522B (en) | 1976-03-15 |
| IL38589A0 (en) | 1972-03-28 |
| HK34278A (en) | 1978-07-07 |
| NO137321B (en) | 1977-10-31 |
| NL7200818A (en) | 1972-07-24 |
| BE778285A (en) | 1972-07-20 |
| FR2122539A1 (en) | 1972-09-01 |
| AU3811072A (en) | 1973-07-26 |
| NL172511B (en) | 1983-04-18 |
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